US20140191222A1 - Resin composition and display device using the same - Google Patents
Resin composition and display device using the same Download PDFInfo
- Publication number
- US20140191222A1 US20140191222A1 US14/202,595 US201414202595A US2014191222A1 US 20140191222 A1 US20140191222 A1 US 20140191222A1 US 201414202595 A US201414202595 A US 201414202595A US 2014191222 A1 US2014191222 A1 US 2014191222A1
- Authority
- US
- United States
- Prior art keywords
- group
- acid
- resin composition
- film
- transmittance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 84
- 229920001721 polyimide Polymers 0.000 claims abstract description 57
- 239000004642 Polyimide Substances 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 49
- 229920005989 resin Polymers 0.000 claims abstract description 49
- 229920002577 polybenzoxazole Polymers 0.000 claims abstract description 31
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 22
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 claims abstract description 13
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims abstract description 11
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims abstract description 11
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 claims abstract description 9
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000010408 film Substances 0.000 claims description 179
- 239000000126 substance Substances 0.000 claims description 58
- 239000000758 substrate Substances 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 230000008859 change Effects 0.000 claims description 26
- 238000010438 heat treatment Methods 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000962 organic group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000002834 transmittance Methods 0.000 abstract description 103
- 239000002243 precursor Substances 0.000 abstract description 45
- 238000001723 curing Methods 0.000 description 89
- -1 quinone diazide compound Chemical class 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 68
- 239000002253 acid Substances 0.000 description 58
- 239000002966 varnish Substances 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 38
- 230000000052 comparative effect Effects 0.000 description 32
- 239000010410 layer Substances 0.000 description 32
- 238000011156 evaluation Methods 0.000 description 29
- 206010034972 Photosensitivity reaction Diseases 0.000 description 27
- 230000036211 photosensitivity Effects 0.000 description 27
- 239000002245 particle Substances 0.000 description 26
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000004952 Polyamide Substances 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 229920002647 polyamide Polymers 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 150000004985 diamines Chemical class 0.000 description 18
- 230000002378 acidificating effect Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- 238000004040 coloring Methods 0.000 description 15
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 15
- 230000009467 reduction Effects 0.000 description 15
- 239000002318 adhesion promoter Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000013019 agitation Methods 0.000 description 13
- 125000004849 alkoxymethyl group Chemical group 0.000 description 13
- 238000011161 development Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 238000001354 calcination Methods 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000003384 imaging method Methods 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000009719 polyimide resin Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 229960005196 titanium dioxide Drugs 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- 238000000411 transmission spectrum Methods 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 125000004427 diamine group Chemical group 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LREMXIQAZBMFIQ-UHFFFAOYSA-N 2-(2-methylphenyl)acetonitrile (2H-thiophen-5-ylideneamino) propane-1-sulfonate Chemical compound CC1=C(C=CC=C1)CC#N.C(CC)S(=O)(=O)ON=C1C=CCS1 LREMXIQAZBMFIQ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 2
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 2
- OLIGPHACAFRDEN-UHFFFAOYSA-N 4-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=C(C2=C(C=CC=C2)C1=O)S(=O)=O OLIGPHACAFRDEN-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- KHLBYJOGKPIERQ-UHFFFAOYSA-N 5-naphthoquinonediazidesulfonyl group Chemical group [N-]=[N+]=C1C=CC2=C(C=CC=C2S(=O)=O)C1=O KHLBYJOGKPIERQ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910003849 O-Si Inorganic materials 0.000 description 2
- 229910003872 O—Si Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 206010040954 Skin wrinkling Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011246 composite particle Substances 0.000 description 2
- 239000011231 conductive filler Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 230000007257 malfunction Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000002971 oxazolyl group Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000005394 sealing glass Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000001039 wet etching Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- AMAJLCUZXGYMRO-UHFFFAOYSA-N (1-hydroxy-2-methylpropan-2-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)CO AMAJLCUZXGYMRO-UHFFFAOYSA-N 0.000 description 1
- RPUUZRPWTIESLW-UHFFFAOYSA-N (1-hydroxy-2-methylpropan-2-yl) prop-2-enoate Chemical compound OCC(C)(C)OC(=O)C=C RPUUZRPWTIESLW-UHFFFAOYSA-N 0.000 description 1
- SGKNPYKCCQCHAE-UHFFFAOYSA-N (1-hydroxy-2-methylpropyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)OC(=O)C(C)=C SGKNPYKCCQCHAE-UHFFFAOYSA-N 0.000 description 1
- RKVMKJUCXYJHEH-UHFFFAOYSA-N (1-hydroxy-2-methylpropyl) prop-2-enoate Chemical compound CC(C)C(O)OC(=O)C=C RKVMKJUCXYJHEH-UHFFFAOYSA-N 0.000 description 1
- PNWODCMQYWCKBF-UHFFFAOYSA-N (2-hydroxy-2-methylpropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)O PNWODCMQYWCKBF-UHFFFAOYSA-N 0.000 description 1
- HSEDDQGMZGGFHS-UHFFFAOYSA-N (2-hydroxy-2-methylpropyl) prop-2-enoate Chemical compound CC(C)(O)COC(=O)C=C HSEDDQGMZGGFHS-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- JKXUAKAQFISCCT-UHFFFAOYSA-M (4-benzoylphenyl)methyl-dimethyl-(2-prop-2-enoyloxyethyl)azanium;bromide Chemical compound [Br-].C1=CC(C[N+](C)(CCOC(=O)C=C)C)=CC=C1C(=O)C1=CC=CC=C1 JKXUAKAQFISCCT-UHFFFAOYSA-M 0.000 description 1
- UROHSXQUJQQUOO-UHFFFAOYSA-M (4-benzoylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].C1=CC(C[N+](C)(C)C)=CC=C1C(=O)C1=CC=CC=C1 UROHSXQUJQQUOO-UHFFFAOYSA-M 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- 0 *C1=CC([3*])=C(O[4*])C([2*])=C1.CC Chemical compound *C1=CC([3*])=C(O[4*])C([2*])=C1.CC 0.000 description 1
- SCEFCWXRXJZWHE-UHFFFAOYSA-N 1,2,3-tribromo-4-(2,3,4-tribromophenyl)sulfonylbenzene Chemical compound BrC1=C(Br)C(Br)=CC=C1S(=O)(=O)C1=CC=C(Br)C(Br)=C1Br SCEFCWXRXJZWHE-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- MKPHQUIFIPKXJL-UHFFFAOYSA-N 1,2-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(O)C(O)OC(=O)C(C)=C MKPHQUIFIPKXJL-UHFFFAOYSA-N 0.000 description 1
- YGJMFYMWJXFBFK-UHFFFAOYSA-N 1,2-dihydroxypropyl prop-2-enoate Chemical compound CC(O)C(O)OC(=O)C=C YGJMFYMWJXFBFK-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- NOVOSPDYVLEEGK-UHFFFAOYSA-N 1,8-diamino-9,9-bis(3-amino-4-hydroxyphenyl)xanthene-2,7-diol Chemical compound NC=1C=C(C=CC=1O)C1(C2=C(C=CC(=C2N)O)OC2=C1C(=C(C=C2)O)N)C1=CC(=C(C=C1)O)N NOVOSPDYVLEEGK-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
- VMCRQYHCDSXNLW-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2-dichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)Cl)C=C1 VMCRQYHCDSXNLW-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- SWWQQSDRUYSMAR-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride Chemical group Cl.C1=CC(O)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 SWWQQSDRUYSMAR-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- QNMHRRCVEGQTPS-UHFFFAOYSA-N 1-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCCC(O)OC(=O)C(C)=C QNMHRRCVEGQTPS-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 description 1
- UXYMHGCNVRUGNO-UHFFFAOYSA-N 1-hydroxypropan-2-yl prop-2-enoate Chemical compound OCC(C)OC(=O)C=C UXYMHGCNVRUGNO-UHFFFAOYSA-N 0.000 description 1
- NUIPOEWADWHGSP-UHFFFAOYSA-N 1-hydroxypropyl 2-methylprop-2-enoate Chemical compound CCC(O)OC(=O)C(C)=C NUIPOEWADWHGSP-UHFFFAOYSA-N 0.000 description 1
- CPWXVNZFDXZIMS-UHFFFAOYSA-N 1-hydroxypropyl prop-2-enoate Chemical compound CCC(O)OC(=O)C=C CPWXVNZFDXZIMS-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- VYMSWGOFSKMMCE-UHFFFAOYSA-N 10-butyl-2-chloroacridin-9-one Chemical compound ClC1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 VYMSWGOFSKMMCE-UHFFFAOYSA-N 0.000 description 1
- SFSLTRCPISPSKB-UHFFFAOYSA-N 10-methylideneanthracen-9-one Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C(=O)C2=C1 SFSLTRCPISPSKB-UHFFFAOYSA-N 0.000 description 1
- PLGAYGHFBSTWCA-UHFFFAOYSA-N 10-phenylsulfanylacridin-9-one Chemical compound C1(=CC=CC=C1)SN1C=2C=CC=CC2C(C2=CC=CC=C12)=O PLGAYGHFBSTWCA-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- AXNALHOLESARRI-UHFFFAOYSA-N 2,3-dihydroxybutyl 2-methylprop-2-enoate Chemical compound CC(O)C(O)COC(=O)C(C)=C AXNALHOLESARRI-UHFFFAOYSA-N 0.000 description 1
- JIFZCWSBRJDZOK-UHFFFAOYSA-N 2,3-dihydroxybutyl prop-2-enoate Chemical compound CC(O)C(O)COC(=O)C=C JIFZCWSBRJDZOK-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- MHDULSOPQSUKBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MHDULSOPQSUKBQ-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- FOLUJWPWRXHMLF-UHFFFAOYSA-N 2-[2-(2-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1C(O)=O FOLUJWPWRXHMLF-UHFFFAOYSA-N 0.000 description 1
- OWDBMKZHFCSOOL-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)propoxy]propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(C)COC(C)COC(=O)C(C)=C OWDBMKZHFCSOOL-UHFFFAOYSA-N 0.000 description 1
- KECOIASOKMSRFT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(O)=CC=2)=C1 KECOIASOKMSRFT-UHFFFAOYSA-N 0.000 description 1
- ZTZLVQYRXBHWEU-UHFFFAOYSA-N 2-amino-4-[1-(3-amino-4-hydroxyphenyl)-9h-fluoren-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C=2C(=C3C(C4=CC=CC=C4C3)=CC=2)C=2C=C(N)C(O)=CC=2)=C1 ZTZLVQYRXBHWEU-UHFFFAOYSA-N 0.000 description 1
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 1
- UZSDRHVOBLQYCX-UHFFFAOYSA-N 2-amino-6-hydroxybenzoic acid Chemical compound NC1=CC=CC(O)=C1C(O)=O UZSDRHVOBLQYCX-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- FLYIRERUSAMCDQ-UHFFFAOYSA-N 2-azaniumyl-2-(2-methylphenyl)acetate Chemical compound CC1=CC=CC=C1C(N)C(O)=O FLYIRERUSAMCDQ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- YMDWIAJIHPMSJF-UHFFFAOYSA-N 2-hydroxybutan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)(O)OC(=O)C(C)=C YMDWIAJIHPMSJF-UHFFFAOYSA-N 0.000 description 1
- IPNCJMYEZCKXIL-UHFFFAOYSA-N 2-hydroxybutan-2-yl prop-2-enoate Chemical compound CCC(C)(O)OC(=O)C=C IPNCJMYEZCKXIL-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- IJOUWMMZJISKHY-UHFFFAOYSA-N 2-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)O IJOUWMMZJISKHY-UHFFFAOYSA-N 0.000 description 1
- OLPSPGUBQWMHJZ-UHFFFAOYSA-N 2-hydroxypropan-2-yl prop-2-enoate Chemical compound CC(C)(O)OC(=O)C=C OLPSPGUBQWMHJZ-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- UPTHZKIDNHJFKQ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane-1,2,3-triol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(O)CO UPTHZKIDNHJFKQ-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical compound O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical group C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 1
- UVNIWYMQSYQAIS-UHFFFAOYSA-N 3-(4-azidophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=CC(=O)C1=CC=CC=C1 UVNIWYMQSYQAIS-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- UCFMKTNJZCYBBJ-UHFFFAOYSA-N 3-[1-(2,3-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)C1=CC=CC(C(O)=O)=C1C(O)=O UCFMKTNJZCYBBJ-UHFFFAOYSA-N 0.000 description 1
- DFSUKONUQMHUKQ-UHFFFAOYSA-N 3-[2-(2,3-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound OC(=O)C1=CC=CC(C(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)(C(F)(F)F)C(F)(F)F)=C1C(O)=O DFSUKONUQMHUKQ-UHFFFAOYSA-N 0.000 description 1
- QMAQHCMFKOQWML-UHFFFAOYSA-N 3-[2-[2-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)S(=O)(=O)C=2C(=CC=CC=2)OC=2C=C(N)C=CC=2)=C1 QMAQHCMFKOQWML-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- GIMFLOOKFCUUOQ-UHFFFAOYSA-N 3-amino-4-hydroxy-1,2-dihydropyrimidin-6-one Chemical compound NN1CN=C(O)C=C1O GIMFLOOKFCUUOQ-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- KFFUEVDMVNIOHA-UHFFFAOYSA-N 3-aminobenzenethiol Chemical compound NC1=CC=CC(S)=C1 KFFUEVDMVNIOHA-UHFFFAOYSA-N 0.000 description 1
- KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 description 1
- DMHHWXWFFRSXQV-UHFFFAOYSA-N 3-hydroxybutan-2-yl 2-methylprop-2-enoate Chemical compound CC(O)C(C)OC(=O)C(C)=C DMHHWXWFFRSXQV-UHFFFAOYSA-N 0.000 description 1
- QXIQCNFSNJEMOD-UHFFFAOYSA-N 3-hydroxybutan-2-yl prop-2-enoate Chemical compound CC(O)C(C)OC(=O)C=C QXIQCNFSNJEMOD-UHFFFAOYSA-N 0.000 description 1
- VHNJXLWRTQNIPD-UHFFFAOYSA-N 3-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(O)CCOC(=O)C(C)=C VHNJXLWRTQNIPD-UHFFFAOYSA-N 0.000 description 1
- JRCGLALFKDKSAN-UHFFFAOYSA-N 3-hydroxybutyl prop-2-enoate Chemical compound CC(O)CCOC(=O)C=C JRCGLALFKDKSAN-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- RSFDFESMVAIVKO-UHFFFAOYSA-N 3-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S)=C1 RSFDFESMVAIVKO-UHFFFAOYSA-N 0.000 description 1
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 1
- FWSFBMFDMJLSPT-UHFFFAOYSA-N 3-tert-butyl-2,6-bis(methoxymethyl)phenol Chemical compound COCC1=C(C(=CC=C1C(C)(C)C)COC)O FWSFBMFDMJLSPT-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- JTWYIRAWVVAUBZ-UHFFFAOYSA-N 4-(4-amino-2,3-dimethylphenyl)-2,3-dimethylaniline Chemical group C1=C(N)C(C)=C(C)C(C=2C(=C(C)C(N)=CC=2)C)=C1 JTWYIRAWVVAUBZ-UHFFFAOYSA-N 0.000 description 1
- GPQSJXRIHLUAKX-UHFFFAOYSA-N 4-(4-amino-2-ethylphenyl)-3-ethylaniline Chemical group CCC1=CC(N)=CC=C1C1=CC=C(N)C=C1CC GPQSJXRIHLUAKX-UHFFFAOYSA-N 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- OUOAFMZIPXCUBR-UHFFFAOYSA-N 4-(4-amino-3,4-dimethylcyclohexa-2,5-dien-1-ylidene)-1,2-dimethylcyclohexa-2,5-dien-1-amine Chemical group C1=CC(N)(C)C(C)=CC1=C1C=C(C)C(C)(N)C=C1 OUOAFMZIPXCUBR-UHFFFAOYSA-N 0.000 description 1
- VLZIZQRHZJOXDM-UHFFFAOYSA-N 4-(4-amino-3-ethylphenyl)-2-ethylaniline Chemical group C1=C(N)C(CC)=CC(C=2C=C(CC)C(N)=CC=2)=C1 VLZIZQRHZJOXDM-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- IJJNNSUCZDJDLP-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJJNNSUCZDJDLP-UHFFFAOYSA-N 0.000 description 1
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 1
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- CCTOEAMRIIXGDJ-UHFFFAOYSA-N 4-hydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)OC2=O CCTOEAMRIIXGDJ-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- JSBBGWWJLQNXNQ-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 JSBBGWWJLQNXNQ-UHFFFAOYSA-N 0.000 description 1
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 1
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 1
- FPKNJPIDCMAIDW-UHFFFAOYSA-N 5-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1C(O)=O FPKNJPIDCMAIDW-UHFFFAOYSA-N 0.000 description 1
- XVOBQVZYYPJXCK-UHFFFAOYSA-N 5-aminonaphthalene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(N)=CC=CC2=C1 XVOBQVZYYPJXCK-UHFFFAOYSA-N 0.000 description 1
- YDEUKNRKEYICTH-UHFFFAOYSA-N 5-aminoquinolin-8-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=N1 YDEUKNRKEYICTH-UHFFFAOYSA-N 0.000 description 1
- NYYMNZLORMNCKK-UHFFFAOYSA-N 5-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1O NYYMNZLORMNCKK-UHFFFAOYSA-N 0.000 description 1
- SMAMQSIENGBTRV-UHFFFAOYSA-N 5-hydroxynaphthalene-2-carboxylic acid Chemical compound OC1=CC=CC2=CC(C(=O)O)=CC=C21 SMAMQSIENGBTRV-UHFFFAOYSA-N 0.000 description 1
- VTUGNNIWJSWUSP-UHFFFAOYSA-N 5-sulfanylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1S VTUGNNIWJSWUSP-UHFFFAOYSA-N 0.000 description 1
- NQSLRCGJQDKCHO-UHFFFAOYSA-N 5-sulfanylnaphthalene-2-carboxylic acid Chemical compound SC1=CC=CC2=CC(C(=O)O)=CC=C21 NQSLRCGJQDKCHO-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- SERBLGFKBWPCJD-UHFFFAOYSA-N 6-aminonaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(N)=CC=C21 SERBLGFKBWPCJD-UHFFFAOYSA-N 0.000 description 1
- CKSZZOAKPXZMAT-UHFFFAOYSA-N 6-aminonaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(N)=CC=C21 CKSZZOAKPXZMAT-UHFFFAOYSA-N 0.000 description 1
- NZTPZUIIYNYZKT-UHFFFAOYSA-N 6-aminonaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(N)=CC=C21 NZTPZUIIYNYZKT-UHFFFAOYSA-N 0.000 description 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
- WSUYONLKFXZZRV-UHFFFAOYSA-N 7-aminonaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(N)=CC=C21 WSUYONLKFXZZRV-UHFFFAOYSA-N 0.000 description 1
- BFBAHPDPLUEECU-UHFFFAOYSA-N 7-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(N)=CC=C21 BFBAHPDPLUEECU-UHFFFAOYSA-N 0.000 description 1
- NBPYPKQPLKDTKB-UHFFFAOYSA-N 7-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(N)=CC=C21 NBPYPKQPLKDTKB-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- OZYYQTRHHXLTKX-UHFFFAOYSA-N 7-octenoic acid Chemical compound OC(=O)CCCCCC=C OZYYQTRHHXLTKX-UHFFFAOYSA-N 0.000 description 1
- ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 8-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C(O)C2=CC(C(=O)O)=CC=C21 ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 0.000 description 1
- PRRFQAVIPFFRRL-UHFFFAOYSA-N 8-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C(S)C2=CC(C(=O)O)=CC=C21 PRRFQAVIPFFRRL-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 1
- 241000202785 Calyptronoma Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QCXXDZUWBAHYPA-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.O=C1NC(=O)NC(=O)N1 Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.O=C1NC(=O)NC(=O)N1 QCXXDZUWBAHYPA-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229910007541 Zn O Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- KLQWZWNTTNRVOZ-UHFFFAOYSA-M [3-(3,4-dimethyl-9-oxothioxanthen-2-yl)oxy-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C1=CC=C2C(=O)C3=CC(OCC(O)C[N+](C)(C)C)=C(C)C(C)=C3SC2=C1 KLQWZWNTTNRVOZ-UHFFFAOYSA-M 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- BRHJUILQKFBMTL-UHFFFAOYSA-N [4,4-bis(dimethylamino)cyclohexa-1,5-dien-1-yl]-phenylmethanone Chemical compound C1=CC(N(C)C)(N(C)C)CC=C1C(=O)C1=CC=CC=C1 BRHJUILQKFBMTL-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- SHPBBNULESVQRH-UHFFFAOYSA-N [O-2].[O-2].[Ti+4].[Zr+4] Chemical compound [O-2].[O-2].[Ti+4].[Zr+4] SHPBBNULESVQRH-UHFFFAOYSA-N 0.000 description 1
- JVQAJHYYWVAKPP-UHFFFAOYSA-N [O-2].[Ti+4].[Sn+2]=O.[O-2].[O-2] Chemical compound [O-2].[Ti+4].[Sn+2]=O.[O-2].[O-2] JVQAJHYYWVAKPP-UHFFFAOYSA-N 0.000 description 1
- IUXAGJRMSWHCIL-UHFFFAOYSA-N [Sn+2]=O.[O-2].[Al+3] Chemical compound [Sn+2]=O.[O-2].[Al+3] IUXAGJRMSWHCIL-UHFFFAOYSA-N 0.000 description 1
- JHGFRCLDPHKRBS-UHFFFAOYSA-N [Sn+2]=O.[O-2].[Zr+4].[O-2].[O-2] Chemical compound [Sn+2]=O.[O-2].[Zr+4].[O-2].[O-2] JHGFRCLDPHKRBS-UHFFFAOYSA-N 0.000 description 1
- JDPAVWAQGBGGHD-UHFFFAOYSA-N aceanthrylene Chemical group C1=CC=C2C(C=CC3=CC=C4)=C3C4=CC2=C1 JDPAVWAQGBGGHD-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- SQFPKRNUGBRTAR-UHFFFAOYSA-N acephenanthrylene Chemical group C1=CC(C=C2)=C3C2=CC2=CC=CC=C2C3=C1 SQFPKRNUGBRTAR-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- JZKNMIIVCWHHGX-UHFFFAOYSA-N adamantane-1,2,2,3-tetracarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)C(C(O)=O)(C(O)=O)C2(C(O)=O)C3 JZKNMIIVCWHHGX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VCRLKNZXFXIDSC-UHFFFAOYSA-N aluminum oxygen(2-) zirconium(4+) Chemical compound [O--].[O--].[Al+3].[Zr+4] VCRLKNZXFXIDSC-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- YUTJCNNFTOIOGT-UHFFFAOYSA-N anthracene-1,8,9-triol Chemical compound C1=CC(O)=C2C(O)=C3C(O)=CC=CC3=CC2=C1 YUTJCNNFTOIOGT-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- TZIQWQARHPGHIG-UHFFFAOYSA-N anthrarobin Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C(O)=C21 TZIQWQARHPGHIG-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- KNNXFYIMEYKHBZ-UHFFFAOYSA-N as-indacene Chemical compound C1=CC2=CC=CC2=C2C=CC=C21 KNNXFYIMEYKHBZ-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- RYJPRVYYQXYKLB-UHFFFAOYSA-N bis(4-benzoyl-4-methylcyclohexa-1,5-dien-1-yl)methanone Chemical compound C1=CC(C)(C(=O)C=2C=CC=CC=2)CC=C1C(=O)C(C=C1)=CCC1(C)C(=O)C1=CC=CC=C1 RYJPRVYYQXYKLB-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000007337 electrophilic addition reaction Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- DDTGNKBZWQHIEH-UHFFFAOYSA-N heptalene Chemical compound C1=CC=CC=C2C=CC=CC=C21 DDTGNKBZWQHIEH-UHFFFAOYSA-N 0.000 description 1
- UJILXQCBVWMDMC-UHFFFAOYSA-N heptane-1,1,1,2-tetracarboxylic acid Chemical compound CCCCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O UJILXQCBVWMDMC-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000006358 imidation reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- YNDRMAAWTXUJPV-UHFFFAOYSA-N n-cyclohexyl-2-methylidenecyclohexan-1-amine Chemical compound C=C1CCCCC1NC1CCCCC1 YNDRMAAWTXUJPV-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical group C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- OVPVGJFDFSJUIG-UHFFFAOYSA-N octalene Chemical compound C1=CC=CC=C2C=CC=CC=CC2=C1 OVPVGJFDFSJUIG-UHFFFAOYSA-N 0.000 description 1
- FMLYSTGQBVZCGN-UHFFFAOYSA-N oxosilicon(2+) oxygen(2-) titanium(4+) Chemical compound [O-2].[Ti+4].[Si+2]=O.[O-2].[O-2] FMLYSTGQBVZCGN-UHFFFAOYSA-N 0.000 description 1
- AXFLWPUWMOTLEY-UHFFFAOYSA-N oxosilicon(2+) oxygen(2-) zirconium(4+) Chemical compound [Si+2]=O.[O-2].[Zr+4].[O-2].[O-2] AXFLWPUWMOTLEY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JRDBISOHUUQXHE-UHFFFAOYSA-N pyridine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)N=C1C(O)=O JRDBISOHUUQXHE-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 description 1
- VHXJRLYFEJAIAM-UHFFFAOYSA-N quinoline-2-sulfonyl chloride Chemical compound C1=CC=CC2=NC(S(=O)(=O)Cl)=CC=C21 VHXJRLYFEJAIAM-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- WEMQMWWWCBYPOV-UHFFFAOYSA-N s-indacene Chemical compound C=1C2=CC=CC2=CC2=CC=CC2=1 WEMQMWWWCBYPOV-UHFFFAOYSA-N 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- H01L27/322—
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
- H10K50/865—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. light-blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/025—Polyamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/027—Polyimide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/035—Ester polymer, e.g. polycarbonate, polyacrylate or polyester
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/06—Substrate layer characterised by chemical composition
- C09K2323/061—Inorganic, e.g. ceramic, metallic or glass
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/18—High density interconnect [HDI] connectors; Manufacturing methods related thereto
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/122—Pixel-defining structures or layers, e.g. banks
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/124—Insulating layers formed between TFT elements and OLED elements
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light
- H10K59/8792—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. black layers
Definitions
- the present invention relates to resin compositions. Particularly, it relates to resin compositions suited for applications such as surface protective films and interlayer dielectric films of semiconductor elements, dielectric layers of organic electroluminescent (hereinafter referred to as EL) elements, planarization films of thin film transistor (hereinafter referred to as TFT) substrates for the driving of display devices using organic EL elements, wire-protecting dielectric films of circuit boards, on-chip microlens of solid imaging elements, planarization films for displays and solid imaging elements, and solder resists for circuit boards.
- resin compositions suited for applications such as surface protective films and interlayer dielectric films of semiconductor elements, dielectric layers of organic electroluminescent (hereinafter referred to as EL) elements, planarization films of thin film transistor (hereinafter referred to as TFT) substrates for the driving of display devices using organic EL elements, wire-protecting dielectric films of circuit boards, on-chip microlens of solid imaging elements, planarization films for displays and solid imaging elements, and solder resist
- Cured films produced by curing compositions containing polyimide or polybenzoxazole have been used widely for dielectric films, protective films, planarization films, and the like of semiconductor elements or display devices. Particularly in display devices, it is required to reduce the transmittance of a cured film in order to increase contrast in applications such as, for example, a dielectric layer of an organic EL display and a black matrix of a liquid crystal display. In order to prevent malfunction caused by penetration of light into a TFT for driving of a display device, a leak electric current, and the like, it is required to reduce the transmittance of a dielectric layer of an organic EL device or a planarization film to be provided on a TFT substrate of an organic EL display.
- Examples of a technology of reducing the transmittance of a visible region greater than a wavelength of 400 nm in a cured film include a method of adding a colorant, such as carbon black, an organic or inorganic pigment, and a dyestuff, to a resin composition like that seen in a black matrix material for liquid crystal displays, an RGB paste material, and the like. Since resin compositions containing such colorants have absorption in a exposure wavelength region of 400 to 450 nm, it is difficult to use them as positive type photosensitive resin compositions which are sensitized by making light reach to a film bottom and therefore the use as a negative type photosensitive resin composition such that a film thereof is photocured from its surface is common.
- a colorant such as carbon black, an organic or inorganic pigment, and a dyestuff
- Examples of a technology of reducing the transmittance of a cured film of a positive type photosensitive resin composition include a positive type radiative resin composition comprising an alkali-soluble resin, a quinone diazide compound, and a coloring composition of a leuco dye, a developing agent, and so on (see, for example, patent document 1), a photosensitive resin in which a heat-sensitive material that will become black upon heating has been added beforehand (see, for example, patent document 2), and a positive type photosensitive resin composition comprising an alkali-soluble resin, a quinone diazide compound, a thermally coloring compound that colors upon heating and exhibits an absorbance maximum at 350 nm or more and 700 nm or less, and a compound that has no absorbance maximum at 350 nm or more and less than 500 nm and has an absorbance maximum at 500 nm or more and 750 nm or less (see, for example, patent document 3).
- Coloring compounds are compounds that will have intramolecular structural change themselves due to heat to develop absorption in a specified wavelength region. Recently, not only coloring compounds but also resin compositions capable of developing absorption in an exposure wavelength region by other means have been demanded in order to improve versatility. Then, an object of the present invention is to provide a resin composition that can reduce the transmittance in the visible region of a cured film by the use of a combination of specific compounds while maintaining the transmittance of the resin film before curing.
- the present invention provides a resin composition
- a resin composition comprising (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, and (c) a thermal cross-linking agent having a structure represented by the following formula (1) or a thermal cross-linking agent having a group represented by the following formula (2):
- R represents a linking group having 2 to 4 valencies
- R 1 represents a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F
- R 2 and R 3 each represent CH 2 OR 5 (R 5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms)
- R 4 represents a hydrogen atom, a methyl group or an ethyl group
- s represents an integer of 0 to 2
- u represents an integer of 2 to 4;
- R 6 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, t is 1 or 2 and v is 0 or 1, provided that t+v is 1 or 2.
- FIG. 1 is a sectional view of a TFT substrate in which a planarization film and a dielectric layer have been formed.
- FIG. 2 is a sectional view of a TFT substrate in which a dielectric layer has been formed.
- FIG. 3 is a transmission spectra of the resin composition of Example 2 before and after curing.
- FIG. 4 is a transmission spectra of the resin composition of Comparative Example 3 before and after curing.
- the resin composition of the present invention comprises (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, and (c) a thermal cross-linking agent having a structure represented by the formula (1) provided above or a thermal cross-linking agent having a group represented by the formula (2) provided above.
- the combination of component (b) and component (c) with the resin of component (a) makes it possible to make a cured film color at 400 to 450 nm to reduce the transmittance in the visible range greatly. Lack of any one of the three compounds (a) to (c) will result in difficulty in the intended coloring at 400 450 nm.
- the components will be described below.
- the resin composition of the present invention includes (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor. It may include two or more of them and also may include a copolymer that has two or more of their repeating units.
- Polyimide and polybenzoxazole are resins that have a cyclic structure of an imide ring or an oxazole ring in their main chain.
- the number of repetitions of the repeating units is preferably 10 to 100000.
- Polyimide can be obtained by reacting a tetracarboxylic acid or its corresponding tetracarboxylic dianhydride or corresponding tetracarboxylic acid diester dichloride with a diamine or its corresponding diisocyanate compound or corresponding trimethylsilylated diamine and it has a tetracarboxylic acid residue and a diamine residue.
- a polyamide acid which is one of the polyimide precursors produced by making a tetracarboxylic dianhydride react with a diamine, by heating treatment or chemical treatment.
- a solvent that azeotropically boils with water such as m-xylene
- the heating treatment may be done at a low temperature of equal to or lower than 100° C. with the addition of a weakly acidic carboxylic acid compound.
- the cyclization catalyst to be used for the chemical treatment include dehydration condensation agents such as carboxylic anhydrides and dicyclohexyl carbodiimide and bases such as triethylamine. A description of the polyimide precursor will be made later.
- Polybenzoxazole can be obtained by making a bisaminophenol compound react with a dicarboxylic acid, its corresponding dicarboxylic acid chloride or corresponding dicarboxylic acid active ester and it has a dicarboxylic acid residue and a bisaminophenol residue.
- a polyhydroxyamide which is one of the polybenzoxazole precursors produced by making a bisaminophenol compound react with a dicarboxylic acid react, by heating treatment or chemical treatment. In the heating treatment, a solvent that azeotropically boils with water, such as m-xylene, may be added.
- the heating treatment may be done at a low temperature of equal to or lower than 200° C. with the addition of an acidic compound.
- the cyclization catalyst to be used for the chemical treatment include phosphoric anhydride, bases, and carbodiimide compounds. A description of the polybenzoxazol precursor will be made later.
- the polyimide preferably has an acidic group or an acidic group derivative such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , in a tetracarboxylic acid residue or a diamine residue, and it more preferably has a hydroxyl group.
- an acidic group or an acidic group derivative such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , in a tetracarboxylic acid residue or a diamine residue, and it more preferably has a hydroxyl group.
- the polybenzoxazole preferably has an acidic group or an acidic group derivative, such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , in a dicarboxylic acid residue or a bisaminophenol residue, and it more preferably has a hydroxyl group.
- R 7 and R 8 each represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- the acidic group refers to a case where all of R 7 or R 8 are hydrogen atoms
- the acidic group derivative refers to a case where a monovalent organic group having 1 to 20 carbon atoms is contained in R 7 or R 8 .
- examples of preferred structures of a tetracarboxylic acid residue of a polyimide and a dicarboxylic acid residue of a polybenzoxazole include structures provided below or structures resulting from replacing 1 to 4 hydrogen atoms of those structures by an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, a fluorine atom, or a chlorine atom. Two or more of these may be used together.
- J represents a direct bond, —COO—, —CONH—, —CH 2 —, and —C 2 H 4 —, —O—, —C 3 H 6 —, —SO 2 —, —S—, —Si(CH 3 ) 2 —, —O—Si(CH 3 ) 2 —O—, —C 6 H 4 —, —C 6 H 4 —O—C 6 H 4 —, —C 6 H 4 —C 3 H 6 —C 6 H 4 —, or —C 6 H 4 —C 3 F 6 —C 6 H 4 —.
- examples of preferred structures of a diamine residue of a polyimide and a bisaminophenol residue of a polybenzoxazole include structures provided below or structures resulting from replacing 1 to 4 hydrogen atoms of those structures by an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, a fluorine atom, or a chlorine atom. Two or more of these may be used together.
- J represents a direct bond, —COO—, —CONH—, —CH 2 —, —C 2 H 4 —, —O—, —C 3 H 6 —, —SO 2 —, —S—, —Si (CH 3 ) 2 —, —O—Si (CH 3 ) 2 —O—, —C 6 H 4 —, —C 6 H 4 —O—C 6 H 4 —, —C 6 H 4 —C 3 H 6 —C 6 H 4 —, or —C 6 H 4 —C 3 F 6 —C 6 H 4 —.
- R 7 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- the polyimide precursor and the polybenzoxazole precursor are resins that have an amide bond in their main chain and are dehydration-cyclized by heating treatment or chemical treatment to become the aforementioned polyimide and polybenzoxazole.
- the number of repetitions of the repeating units is preferably 10 to 100000.
- the polyimide precursor include a polyamide acid, a polyamide acid ester, a polyamide acid amide, and a polyisoimide, and a polyamide acid and a polyamide acid ester are preferred.
- the polybenzoxazole precursor include a polyhydroxyamide, a polyaminoamide, polyamide, and a polyamide-imide, and a polyhydroxyamide is preferred.
- the polyimide precursor and the polybenzoxazole precursor preferably have an acidic group or an acidic group derivative such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , in an acid residue or an amine residue, and they more preferably have a hydroxyl group.
- R 7 and R 8 represent hydrogen atoms or monovalent organic groups having 1 to 20 carbon atoms.
- the acidic group refers to a case where all of R 7 or R 8 are hydrogen atoms
- the acidic group derivative refers to a case where a monovalent organic group having 1 to 20 carbon atoms is contained in R 7 or R 8 .
- examples of a dicarboxylic acid include terephthalic acid, isophthalic acid, diphenylether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenone dicarboxylic acid, and triphenyldicarboxylic acid.
- a tricarboxylic acid include trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid.
- tetracarboxylic acid examples include aromatic tetracarboxylic acids, such as pyromellitic acid, 3,3′,4,4′-biphenyl tetracarboxylic acid, 2,3,3′,4′-biphenyl tetracarboxylic acid, 2,2′,3,3′-biphenyl tetracarboxylic acid, 3,3′,4,4′-benzophenonetetracarboxylic acid, 2,2′,3,3′-benzophenone tetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane, bis
- dicarboxylic acids, tricarboxylic acids or tetracarboxylic acids provided above as examples whose 1 to 4 hydrogen atoms have been substituted with an acidic group or acidic group derivative, such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , preferably with a hydroxyl group, a sulfonic acid group, a sulfonic acid amide group, or a sulfonic acid ester group.
- silicon atom-containing tetracarboxylic acid such as dimethylsilanediphthalic acid and 1,3-bis(phthalic acid)tetramethyldisiloxane
- a silicon atom-containing tetracarboxylic acid such as dimethylsilanediphthalic acid and 1,3-bis(phthalic acid)tetramethyldisiloxane
- These silicon atom-containing tetracarboxylic acids are preferably used in 1 to 30 mol % of the whole acid component.
- diamine component that constitutes the amine residue of the polyimide precursor and the polybenzoxazole precursor examples include hydroxyl group-containing diamines, such as bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, bis(3-amino-4-hydroxy)biphenyl, bis(3-amino-4-hydroxyphenyl)fluorene, carboxyl group-containing diamines, such as 3,5-diaminobenzoic acid and 3-carboxy-4,4′-diaminodiphenyl ether, sulfonic acid-containing diamines, such as 3-sulfonic acid-4,4-diaminodiphenyl ether, dithio
- these diamines may be substituted with an alkyl group having 1 to 10 carbon atoms, such as a methyl group and an ethyl group, a fluoroalkyl group having 1 to 10 carbon atoms, such as a trifluoromethyl group, or a group such as F, Cl, Br, and I. Two or more of these may be used together.
- an aromatic diamine in 50 mol % or more of the whole diamine.
- the diamines provided above as examples preferably have an acidic group or an acidic group derivative, such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , and they more preferably have a hydroxyl group.
- an acidic group or an acidic group derivative such as OR 7 , SO 3 R 7 , CONR 7 R 8 , COOR 7 , and SO 2 NR 7 R 8 , and they more preferably have a hydroxyl group.
- diamines can be used as they are or in the form of a corresponding diisocyanate compound or trimethylsilylated diamine.
- silicon atom-containing diamine such as 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 1,3-bis(4-anilino)tetramethyldisiloxane
- a diamine component can enhance adhesion property to a substrate or resistance to oxygen plasma to be used for washing and resistance to a UV ozone treatment.
- These silicon atom-containing diamines are preferably used in 1 to 30 mol % of the whole diamine component.
- a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor with a monoamine having a hydroxyl group, a carboxyl group, a sulfonic acid group, or a thiol group, an acid anhydride, an acid chloride, or a monocarboxylic acid. Two or more of these may be used together.
- the dissolution rate of a resin to an aqueous alkali solution can be adjusted easily to a preferable range by the possession of the aforementioned group at a resin end.
- a monoamine examples include 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 2-aminobenzenesulfonic acid, 3-aminobenzo
- the acid anhydride, the monoacid chloride, the monocarboxylic acid, and the mono-active ester compound include acid anhydrides, such as phthalic anhydride, maleic anhydride, nasic acid, cyclohexane dicarboxylic acid anhydride, and 3-hydroxyphthalic acid anhydride; monocarboxylic acids, such as 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, and 4-carboxybenzenesulfonic acid, and monoacid chloride compounds resulting from conversion of their carboxyl groups to
- the content of the end-capping agent such as the aforementioned monoamine, acid anhydride, acid chloride, and monocarboxylic acid, is preferably within a range of 0.1 to 60 mol %, more preferably from 5 to 50 mol %, of the number of moles of the charged acid component monomer to constitute an acid residue or the charged diamine component monomer to constitute an diamine residue.
- the resin also may have a polymerizable functional group at its end.
- the polymerizable functional group include an ethylenically unsaturated linking group, anacetylene group, a methylol group, and an alkoxymethyl group.
- the end-capping agent having been introduced into a resin can be detected easily by the following method.
- an end-capping agent can be detected easily by dissolving a resin into which the end-capping agent has been introduced in an acidic solution to decompose the resin into an amine component and an acid component which are constitutional units of the resin, and then measuring them by gas chromatography (GC) or NMR.
- GC gas chromatography
- NMR nuclear magnetic resonance
- a polyimide precursor or a polybenzoxazole precursor is preferred as component (a) and a polyimide precursor is more preferred.
- a polyimide precursor advances an imidation reaction in which an amide acid moiety is cyclized by curing calcination at about 200° C.
- a polybenzoxazole precursor advances an oxazolation reaction in which a hydroxyamide moiety is cyclized by curing calcination at about 300° C., resulting in remarkable improvement in chemical resistance.
- the polyimide precursor makes it possible to obtaine chemical resistance at a lower calcination temperature.
- a photosensitive resin composition using such a precursor resin having a property to volumetrically shrink at the time of curing calcination makes it possible to obtain a pattern in a forward-tapered form by obtaining a fine pattern by an exposure-development step and then performing calcination.
- This pattern in a forward-tapered form is superior in ability to cover an upper electrode when being used as a dielectric film of an organic EL element, and it can prevent breakage of wiring and can improve the reliability of an element.
- the resin composition of the present invention may contain alkali-soluble resins other than component (a).
- An alkali-soluble resin refers to any resin having an acidic group to become soluble in alkali and specific examples thereof include radically polymerizable polymers having acrylic acid, a phenol novolak resin, and polyhydroxystyrene, polysiloxane. It is also permitted to adjust the alkali solubility by protecting the acidic groups of these resins.
- Such a resin is a substance that is soluble in an aqueous solution of an alkali, such as choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate as well as tetramethylammonium hydroxide.
- an alkali such as choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate as well as tetramethylammonium hydroxide.
- the resin composition of the present invention contains (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene. Two or more of these may be contained.
- the possession of two hydroxyl groups results in better alkali developability in comparison to a case of possessing one hydroxyl group and can improve photosensitivity.
- the naphthalene structure which is a fused polycyclic structure, is higher in electron density than a monocyclic compound and it comes to have an increased electron density through its possession of two hydrogen groups and can effectively cause an electrophilic addition reaction of a thermal cross-linking agent (c) described later.
- the conjugation of n-electrons is prone to spread in two or more directions to develop color after the formation of a cross-linking reaction, and therefore, it is possible to greatly reduce the transmittance in the visible region of a cured film by combining it with a thermal cross-linking agent (c) described later.
- a thermal cross-linking agent (c) described later.
- Such an effect becomes particularly remarkable when the structure has hydroxyl groups at 1,5-positions, 1,6-positions, 1,7-positions, or 2,3-positions.
- a cross-linking reaction of the thermal cross-linking agent (c) and the above-mentioned component (a) it is possible to fix the compound of component (b) to component (a), which is superior in heat resistance, so that the chemical resistance of a cured film can be improved.
- the resin composition of the present invention may contain, in addition to (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, another fused polycyclic aromatic compound having two or more hydroxyl groups.
- Examples of the skeleton structure of the fused polycyclic aromatic compound having two or more hydroxyl groups include carbon fused bicyclic structure, such as pentalene, indene, naphthalene, azulene, heptalene, and octalene, carbon fused tricyclic structure, such as as-indacene, s-indacene, biphenylene, acenaphthylene, fluorene, phenanthrene, and anthracene, carbon fused tetracyclic structure, such as trindene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, tetraphene, and naphthacene, and carbon fused pentacyclic structure, such as picene, perylene, pentaphene, pentacene, and tetraphenylene.
- carbon fused pentacyclic structure
- a heterocyclic structure containing nitrogen, sulfur, or oxygen atoms instead of some carbon atoms of the aforementioned carbon fused polycyclic aromatic compounds is also available.
- the fused polycyclic aromatic heterocompound include fused heterobicyclic compounds, such as benzofuran, benzothiophene, indole, benzimidazole, benzothiazole, purine, quinoline, isoquinoline, cinnoline, and quinoxaline, and fused heterotricyclic compounds, such as dibenzofuran, carbazole, acridine, and 1,10-phenanthroline.
- Compounds each resulting from replacing some hydrogen atoms of a compound having a skeleton provided above as an example by two or more hydroxyl groups are preferred as the fused polycyclic aromatic compound having two or more hydroxyl groups.
- fused polycyclic aromatic compound having two or more hydroxyl groups include 1,4-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,4-dihydroxyquinoline, 2,6-dihydroxyquinoline, 2,3-dihydroxyquinoxaline, anthracene-1,2,10-triol, and anthracene-1,8,9-triol.
- the content of (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, or 1,7-dihydroxynaphthalene is preferably 5 parts by weight or more, more preferably 10 parts by weight or more relative to 100 parts by weight of the resin of component (a). It is preferably 120 parts by weight or less, and more preferably 100 parts by weight or less. If the content of component (b) is 5 parts by weight or more, the transmittance in the visible region of a cured film can be reduced more. If it is 120 parts by weight or less, it is possible to maintain the strength of a cured film and reduce the percentage of water absorption. When containing two or more kinds of component (a) or component (b), their total amount is preferably within the above-mentioned range.
- the resin composition of the present invention contains (c) a thermal cross-linking agent having a structure represented by the following formula (1) or a thermal cross-linking agent having a group represented by the following formula (2). Two or more of these may be contained.
- the thermal cross-linking agent of component (c) can reduce the transmittance of the visible range greatly by cross-linking itself to both (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, and (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, thereby linking the three components (a), (b), and (c) together. Moreover, it can increase the chemical resistance of a cured film through a cross-linking reaction.
- R represents a linking group having 2 to 4 valencies.
- R 1 represents a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F.
- Monovalent hydrocarbon groups having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group, are preferred as the monovalent organic group having 1 to 20 carbon atoms.
- R 2 and R 3 each represent CH 2 OR 5 (R 5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms).
- R 4 represents a hydrogen atom, a methyl group or an ethyl group. s represents an integer of 0 to 2 and u represents an integer of 2 to 4. A plurality of R 1 s is to R 4 s each may be the same or different. Examples of the linking group R are provided below.
- R 9 to R 27 each represent a hydrogen group, a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F.
- a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, a cyclohexyl group, a benzyl group, and a naphthyl group are preferred as the monovalent organic group having 1 to 20 carbon atoms.
- R 6 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms.
- t represents 1 or 2 and v represents 0 or 1, provided that t+v is 1 or 2.
- R 2 and R 3 each represent a thermally cross-linkable group, CH 2 OR 5 (R 5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms).
- R 5 is preferably a monovalent hydrocarbon group having 1 to 4 carbon atoms because it leaves a moderate reactivity and excels in storage stability.
- R 5 is more preferably a methyl group or an ethyl group.
- the number of the functional groups of the thermally cross-linkable groups accounting for in one molecule is 4 to 8. If the number of the functional groups is less than 4, it is impossible to color the resin composition after curing moderately and also impossible to reduce the transmittance in the visible region of a cured film. On the other hand, if the number of the functional groups exceeds 8, it is difficult to obtain a compound that is high in purity and the stability of the compound itself and the storage stability in a resin composition deteriorate.
- the purity of the compound having a structure represented by formula (1) is preferably 75% or more, and more preferably 85% or more. If the purity is 85% or more, the storage stability is good, a cross-linking reaction of a resin composition is fully carried out, resulting in a superior coloring property after curing, and it is possible to reduce the transmittance in the visible region of a cured film. Since it is possible to reduce unreacted groups, that serve as water-absorptive groups, it is possible to reduce the water absorptivity of a resin composition. Examples of the method for obtaining a thermal cross-linking agent having a high purity include recrystallization and distillation. The purity of the thermal cross-linking agent can be determined by liquid chromatography.
- thermal cross-linking agent having a structure represented by formula (1) are given below.
- R 6 which is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, preferably is a monovalent hydrocarbon group having 1 to 4 carbon atoms. From the viewpoint of the stability of a compound or the storage stability in a resin composition, it is preferred, in a photosensitive resin composition containing a photo acid generator, a photopolymerization initiator, or the like, that R 6 be a methyl group or an ethyl group and it is preferred that the number of the (CH 2 OR 6 ) groups contained in the compound be 8 or less.
- the content of (c) the thermal cross-linking agent having a structure represented by formula (1) or the thermal cross-linking agent having a group represented by formula (2) is preferably 5 parts by weight or more and more preferably is 10 parts by weight or more relative to 100 parts by weight of the resin of component (a). It is preferably 120 parts by weight or less, and more preferably 100 parts by weight or less. If the content of component (c) is 5 parts by weight or more, the transmittance in the visible region of a cured film can be reduced more. If it is 120 parts by weight or less, the strength of a cured film is high and also the resin composition is superior in storage stability. When containing two or more kinds of component (a) or component (c), their total amount is preferably within the above-mentioned range.
- the resin composition of the present invention may further comprise (d) a photo acid generator, or (e) a photopolymerization initiator and (f) a compound having two or more ethylenically unsaturated bonds and can impart positive type or negative type photosensitivity.
- the photo acid generator Due to the inclusion of (d) the photo acid generator in the resin composition of the present invention, an acid is generated by in a part exposed to light, so that the solubility of a part exposed to light in an aqueous alkali solution increases and a positive type relief pattern in which the part exposed to light dissolves can be obtained. Moreover, the inclusion of (d) the photo acid generator and an epoxy compound makes it possible to obtain a negative type relief pattern in which acids generated in a part exposed to light promotes the reaction of the epoxy compound, so that the part exposed to light becomes insoluble.
- Examples of (d) the photo acid generator include quinone diazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts.
- Examples of the quinone diazide compound include a compound in which the sulfonic acid of quinone diazide has been bonded to a polyhydroxy compound via an ester, a compound in which the sulfonic acid of quinone diazide has been sulfonamide-bonded to a polyamino compound, and a compound in which the sulfonic acid of quinone diazide has been ester-bonded and/or sulfonamide-bonded to a polyhydroxypolyamino compound. It is preferred that 50 mol % or more of the whole functional groups of such a polyhydroxy compound or polyamino compound have been substituted with quinone diazide. It is preferred that two or more kinds of photo acid generators (d) be contained and a highly photosensitive resin composition can be obtained.
- a naphthoquinonediazide sulfonyl ester compound that has a 4-naphthoquinone diazide sulfonyl group and a 5-naphthoquinone diazide sulfonyl group in the same molecule may be contained, and both a 4-naphthoquinonediazide sulfonyl ester compound and a 5-naphthoquinonediazide sulfonyl ester compound may be contained.
- sulfonium salt phosphonium salts, diazonium salts are preferred because they moderately stabilize the acid component generated by exposure to light.
- sulfonium salts are preferred.
- the content of the photo acid generator (d) is preferably 0.01 to 50 parts by weight relative to 100 parts by weight of the resin of component (a).
- the range of 3 to 40 parts by weight is preferred for a quinone diazide compound.
- the total amount of the sulfonium salt, the phosphonium salt, and the diazonium salt is preferably within the range of 0.5 to 20 parts by weight.
- a sensitizing agent or the like can also be contained according to need. When containing two or more kinds of component (d), their total amount is preferably within the above-mentioned range.
- the photosensitive resin composition of the present invention may further comprise (e) a photopolymerization initiator and (f) a compound having two or more ethylenically unsaturated bonds. It is possible to obtain a negative type relief pattern in which active radicals generated in the part exposed to light advance the radical polymerization of ethylenically unsaturated bonds, so that the part exposed to light becomes insoluble.
- Examples of (e) the photopolymerization initiator include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexyl-phenyl ketone, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, 2-methyl-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzophenone, methyl o-benzo
- the content of the photopolymerization initiator (e) is preferably 0.1 to 20 parts by weight relative to 100 parts by weight of the resin of component (a). If it is 0.1 parts by weight or more, a sufficient amount of radical is generated by irradiation with light and photosensitivity increases. If it is 20 parts by weight or less, curing of a part unexposed to light caused by the generation of excessive radicals does not occur, resulting in increase in alkali developability. When containing two or more kinds of component (e), their total amount is preferably within the above-mentioned range.
- Examples of the compound having two or more ethylenically unsaturated bonds (f) include acrylic monomers such as ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate, trimethylolpropane triacrylate, ethoxylated bisphenol A dimethacrylate, glycerin dimethacrylate, tripropylene glycol dimethacrylate, butanediol dimethacrylate, glycerin triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated pentaerythritol tetraacrylate, and ethoxylated isocyanuric acid triacrylate. Two or more of these may be contained.
- the content of the compound having two or more ethylenically unsaturated bonds (f) is preferably 1 part by weight or more, and more preferably 5 parts by weight of more relative to 100 parts by weight of the resin of component (a). It is preferably 100 parts by weight or less, and more preferably 50 parts by weight or less.
- their total amount is preferably within the above-mentioned range.
- a compound having only one ethylenically unsaturated bond may be contained in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the resin of component (a).
- examples of such a compound include acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, dimethylacrylamide, dimethylaminoethyl methacrylate, acryloylmorpholin, 1-hydroxyethyl alpha-chloroacrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl ⁇ -chloroacrylate, 1-hydroxypropyl methacrylate, 1-hydroxypropyl acrylate, 1-hydroxypropyl ⁇ -chloroacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl ⁇ -chloroacrylate, 2-hydroxypropyl meth
- the resin composition of the present invention may further contain (g) a thermal acid generator.
- the thermal acid generator (g) generates an acid on heating after development described later, so that it promotes a cross-linking reaction of the resin of component (a) with the thermal cross-linking agent of component (c) and also promotes the cyclization of the imide ring or the oxazole ring of the resin of component (a). This offers the improvement in chemical resistance of a cured film and successfully reduces film loss.
- the acid to be generated from the thermal acid generator (g) is preferably a strong acid and, for example, aryl sulfone acids, such as p-toluenesulfonic acid and benzenesulfonic acid, and alkyl sulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, and butanesulfonic acid, are preferred.
- the thermal acid generator preferably is an aliphatic sulfonic acid compound represented by formula (4) or (5) and it may contain two or more kinds of such compounds.
- R 30 to R 32 each represent an alkyl group having 1 to 10 carbon atoms or a monovalent aromatic group having 7 to 12 carbon atoms.
- the alkyl group and the aromatic group may be substituted and examples of a substituent include an alkyl group and a carbonyl group.
- the content of the thermal acid generator (g) is preferably 0.1 parts by weight or more, more preferably 0.3 parts by weight or more, and even more preferably 0.5 parts by weight or more relative to 100 parts by weight of the resin of component (a).
- the content of the thermal acid generator (g) is preferably 20 parts by weight or less, more preferably 15 parts by weight or less, and even more preferably 10 parts by weight or less.
- the resin composition of the present invention can contain (h) a filler.
- a filler In the case of using the resin composition of the present invention as a solder resist for circuit boards, the inclusion of the filler (h) has an effect of exhibiting thixotropy to maintain a pattern at a prescribed size in the course of coating the composition by screen printing and drying it. Moreover, an effect to control shrinkage caused by heat curing is also expectable.
- examples of insulative fillers include calcium carbonate, silica, alumina, aluminum nitride, titanium oxide, andsilica-titaniumoxide composite particles, and silica, titanium oxide, and silica-titanium oxide composite particles are preferred.
- examples of the electrically conductive filler include gold, silver, copper, nickel, aluminum, and carbon, and silver is preferred. Two or more of these may be contained depending upon the intended application.
- the content of the filler (h) is preferably within the range of 5 to 500 parts by weight relative to 100 parts by weight of component (a).
- the number average particle diameter of the filler (h) is preferably 10 ⁇ m or less and more preferably 2 ⁇ m or less. The use of two or more fillers differing in number average particle diameter in combination is also preferred from the viewpoint of imparting thixotropy and stress relaxation.
- nanoparticles particles having a number average particle diameter of 100 nm or less, which are so-called nanoparticles, as the filler (h) makes it possible to adjust physical properties such as index of refraction while maintaining light transmittance.
- the use of nanoparticles with a high index of refraction makes it possible to develop a high transmittance and a high index of refraction simultaneously.
- the mixing of such nanoparticle makes it possible to be used suitably as a low-temperature-curable optical thin film, such as an on-chip microlens of a solid imaging element and a planarization film for displays and solid imaging elements.
- particles suitable for the above-mentioned purpose include tin oxide-aluminum oxide mixed particles, zirconium oxide-aluminum oxide mixed particles, zirconium oxide-silicon oxide mixed particles, tin oxide particles, zirconium oxide-tin oxide mixed particles, titanium oxide particles, tin oxide-titanium oxide mixed particles, silicon oxide-titanium oxide mixed particles, zirconium oxide-titanium oxide mixed particles, and zirconium oxide particles.
- the surface of particles may be coated with another substance.
- the above-mentioned particles may be either in the form of a powder or in the form of sol, they are preferably in the form of sol from the viewpoint of easiness with which they are dispersed.
- the number average particle diameter of the nanoparticles is preferably 50 nm or less and more preferably 30 nm or less.
- the number average particle diameter of a filler can be measured by using various particle counters.
- the average particle diameter of nanoparticles can be measured by, for example, a gas adsorption method, a dynamic light scattering method, an X-ray small angle scattering method, or a method of measuring particle diameters directly with a transmission electron microscope.
- the particle diameter obtained by these measuring methods may be in volume average or in mass average, it can be converted into a number average molecular weight with the assumption that the shape of a particle is spherical.
- the resin composition of the present invention can contain a thermally coloring compound that colors on heating to exhibit an absorbance maximum at 350 nm or longer and 700 nm or shorter or an organic pigment or dyestuff that has no absorbance maximum at 350 nm or longer and shorter than 500 nm and has an absorbance maximum at 500 nm or longer and 750 nm or shorter.
- the coloring temperature of the thermally coloring compound is preferably 120° C. or higher and more preferably is 150° C. or higher. The heat resistance under high temperature conditions becomes better and the light resistance becomes better without the occurrence of fading due to prolonged ultraviolet-visible light irradiation as the coloring temperature of the thermally coloring compound becomes higher.
- thermally coloring compound examples include heat-sensitive dyes, pressure-sensitive dyes, and hydroxyl group-containing compounds having a triarylmethane skeleton.
- the resin composition of the present invention may contain an adhesion promoter.
- adhesion promoter include silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimetoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryl trimethoxysilane, 3-aminopropyl trimethoxysilane, 3-aminopropyltriethoxysilane, and N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, compounds to be obtained by reacting an aromatic amine compound with an alkoxy group-containing silicon compound.
- adhesive promoters can enhance the adhesion property with a base substrate, such as a silicon wafer, ITO, SiO 2 , and silicon nitride, when, for example, developing a photosensitive resin film. Moreover, it is possible to enhance resistance to oxygen plasma and UV ozone treatment to be used for washing or the like.
- the content of the adhesion promoter is preferably 0.1 to 10 parts by weight per 100 parts by weight of the resin of component (a).
- the resin composition of the present invention may contain an adhesion promoter.
- the adhesion promoter include alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, and non-aromatic silane compounds. Two or more of these may be contained. Inclusion of such compounds can improve the adhesive property with a substrate after curing.
- Specific examples of the alkoxysilane-containing aromatic amine compounds and aromatic amide compounds are provided below.
- compounds obtainable by reacting an aromatic amine compound with an alkoxy group-containing silicon compound can also be used and examples thereof include compounds obtainable by reacting an aromatic amine compound with an alkoxysilane compound has a group that reacts with an amino group, such as an epoxy group and a chloromethyl group.
- non-aromatic silane compounds include vinyl silane compounds, such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyl trichlorosilan, and vinyltris( ⁇ -methoxyethoxy)silane, and carbon-carbon unsaturated bond-containing silane compounds, such as 3-methacryloxypropyltrimethoxysilane, 3-acryloxyprophyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane.
- vinyltrimethoxysilane and vinyltriethoxysilane are preferred.
- the total content of the alkoxysilane-containing aromatic amine compound, the aromatic amide compound, or the non-aromatic silane compound is preferably 0.01 to 15 parts by weight relative to 100 parts by weight of the resin of component (a).
- the resin composition of the present invention may contain a surfactant, by which the wettability with a substrate can be improved.
- the surfactant examples include fluorine-based surfactants, such as Fluorad (commercial name, available from Sumitomo 3M Ltd.), MEGAFAC (commercial name, available from DIC Corporation), and Sulfron (commercial name, available from Asahi Glass Co., Ltd.), organic siloxane surfactants, such as KP341 (commercial name, available from Shin-Etsu Chemical Co., Ltd.), DBE (commercial name, Chisso Corporation), POLYFLOW, GLANOL (commercial names, available from Kyoeisha Chemical Co., Ltd.), and BYK (available from BYK-Chemie), and acrylic polymer surfactants, such as POLYFLOW (commercial name, available from Kyoeisha Chemical Co., Ltd.).
- fluorine-based surfactants such as Fluorad (commercial name, available from Sumitomo 3M Ltd.), MEGAFAC (commercial name, available from DIC Corporation), and Sulfron (commercial name, available from Asahi Glass Co.
- the resin composition of the present invention preferably contains a solvent.
- the solvent include polar aprotic solvents, such as N-methyl-2-pyrrolidone, ⁇ -butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide, ethers, such as tetrahydrofuran, dioxane, propylene glycol monomethyl ether, and propylene glycol monoethyl ether, ketones, such as acetone, methyl ethyl ketone, diisobutyl ketone, and diacetone alcohol, esters, such as ethyl acetate, butyl acetate, isobutyl acetate, propyl acetate, propylene glycol monomethyl ether acetate, and 3-methyl-3-methoxy butyl acetate, alcohols, such as ethyl lactate, methyl lactate, diacetone alcohol, and 3-methyl-3-
- the transmittance of a resin film before curing be high and the transmittance in the visible region of a cured film be low.
- the change in transmittance at a wavelength of 450 nm before and after curing in a 3.0 ⁇ m thick film be 20% or more.
- the transmittance at a wavelength of 450 nm is an index of the transmittance in the visible region.
- the transmittance change be 20% or more, which is calculated by the following formula from the transmittance at a wavelength of 450 nm of a 3.0 ⁇ m thick film (before curing) to be obtained by coating a resin composition to a substrate and then heat-treating it at 120° C. for 2 minutes and the transmittance at a wavelength of 450 nm of a 3.0 ⁇ m thick film (after curing) to be obtained by further heat-treating the film before curing, at 230° C. for 30 minutes under nitrogen flow.
- the present invention makes it possible to realize such a change in transmittance easily.
- the transmittance of a resin film before curing be high. Specifically, the transmittance at a wavelength of 450 nm of a resin film before curing is preferable 70% or more and more preferably 90% or more. It is preferred that the transmittance in the visible region of a cured film be low. Specifically, the transmittance at a wavelength of 450 nm of a cured film is preferable 70% or less and more preferably 60% or less.
- the change in transmittance at a wavelength of 450 nm before and after curing is preferably 20% to 100% and more preferably 30% to 100%.
- a resin composition can be obtained by dissolving the aforementioned components (a) to (c) and, if necessary, components (d) to (h), a thermally coloring component, an adhesion promoter, an adhesion promoter, a surfactant, or the like in a solvent.
- the dissolving method include agitation and heating. In the case of heating, it is preferred to adjust the heating temperature as far as the performance of a resin composition is not impaired and it is usually from room temperature to 80° C.
- the order of dissolving components is not particularly limited and, for example, there is method of dissolving them one after another from a compound lower in solubility.
- the hole diameter of the filter is, for example, but is not limited to, 0.5 ⁇ m, 0.2 ⁇ m, 0.1 ⁇ m, and 0.05 ⁇ m.
- Examples of the material of the filter includepolypropylene (PP), polyethylene (PE), nylon (NY), and polytetrafluoroethylene (PTFE), and polyethylene and nylon are preferred.
- PP polypropylene
- PE polyethylene
- NY nylon
- PTFE polytetrafluoroethylene
- polyethylene and nylon are preferred.
- the resin composition contains (h) a filler or an organic pigment, it is preferred to use a filter having a pore diameter larger than the particle diameter of them.
- a resin composition film is obtained by coating the resin composition of the present invention by a spin coating method, a slit coating method, a dip coating method, a spray coating method, a printing method, or the like.
- the substrate to which the resin composition is to be coated may be pretreated with the adhesion promoter mentioned above.
- a method of treating a substrate surface by using a solution in which 0.5 to 20% by weight of an adhesion promoter has been dissolved in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and diethyl adipate.
- a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and diethyl adipate.
- the method of treating the substrate surface include spin coating, slit die coating, bar coating, dip coating, spray coating, and vapor treatment. According to need, it is permitted to advance a reaction between the substrate and the adhesion promoter by conducting drying treatment under reduced pressure and then conducting heat treatment of 50° C. to 300° C
- a cured film can be obtained by thermally treating a resulting resin composition film.
- a method of performing heat treatment at 230° C. for 60 minutes, a method of performing heat treatment at 120 to 400° C. for 1 minute to 10 hours, a method of performing heat treatment at a low temperature of from room temperature to about 100° C. with addition of a curing catalyst or the like, and a method of performing curing at a low temperature of from room temperature to about 100° C. by a supersonic wave or electromagnetic wave treatment are mentioned.
- a negative type or positive type relief pattern can be obtained by irradiating the above-mentioned resin composition film partially with active light, such as an ultraviolet ray, and performing developing treatment with a developing solution.
- a cured film obtained by curing the resin composition of the present invention is suitably used as a dielectric film or a protective film of wires.
- a dielectric film or a protective film of wires in a printed board in which wires are formed from copper, aluminum, or the like on a film or a substrate of a polyimide and ceramics, and an application for a protective film for partly soldering wires.
- the resin composition contains an electrically conductive filler, it can also be used as a wire material.
- a cured film obtained by curing the resin composition of the present invention is suitably used as a planarization film or a dielectric layer of a display device having a substrate with a TFT formed thereon, a planarization film, a dielectric layer, and a display element in this order.
- Examples of a display device of this constitution include a liquid crystal display device and an organic EL display device.
- An active matrix type display device has a TFT on a substrate of glass or the like and wires located in a side portion of the TFT and connected to the TFT and has a planarization film thereon so that it may cover the irregularities of the wires, and it is further provided with a display element on the planarization film.
- FIG. 1 shows a sectional view of a TFT substrate in which a planarization film and a dielectric layer have been formed.
- a bottom gate type or top gate type TFT 1 in matrix form has been provided on a substrate 6 and a dielectric film 3 has been formed with the TFT 1 covered therewith.
- a wire 2 connected to the TFT 1 has been provided under the dielectric film 3 .
- a contact hole that opens the wire 2 and a planarization film 4 with the wire and the contact hole embedded.
- the planarization film 4 has been provided with an opening so as to reach the contact hole 7 of the wire 2 .
- an ITO (transparent electrode) 5 has been formed on the planarization film 4 in connection with the wire 2 via the contact hole 7 .
- the ITO 5 serves as an electrode of a display element (for example, organic EL element).
- a dielectric layer 8 is formed so that the periphery of the ITO 5 may be covered.
- This organic EL element may be either a top emission type which emits light from the side opposite to the substrate 6 or a bottom emission type which extracts light from the side of the substrate 6 .
- an active matrix type organic EL display device in which the organic EL elements each have been connected to a TFT 1 for driving them.
- a cured film obtained by curing the resin composition of the present invention is suitably used as a dielectric layer of a display device having a substrate with a TFT formed thereon, a dielectric layer, and a display element in this order.
- Examples of a display device having such a constitution include organic EL display devices.
- An active matrix type display device has a TFT on a substrate of glass or the like, and wires located in a side part of the TFT and connected to the TFT. The display element and the wires are connected via a contact hole formed in the dielectric film.
- FIG. 2 shows a sectional view of a TFT substrate in which a dielectric layer has been formed.
- a bottom gate type or top gate type TFT 1 in matrix form has been provided on a substrate 6 and a dielectric film 3 has been formed with the TFT 1 covered therewith.
- a wire 2 connected to the TFT 1 has been provided under the dielectric film 3 .
- a contact hole 7 has been formed on the dielectric film 3 so that it may open the wire 2 .
- An ITO (transparent electrode) 5 has been formed in connection with the wire 2 via the contact hole 7 .
- the ITO 5 serves as an electrode of a display element (for example, organic EL element).
- a dielectric layer 8 is formed so that the periphery of the ITO 5 , the TFT, and the steps of the wires may be covered.
- This organic EL element may be either a top emission type which emits light from the side opposite to the substrate 6 or a bottom emission type which extracts light from the side of the substrate 6 .
- an active matrix type organic EL display device in which the organic EL elements each have been connected to a TFT 1 for driving them.
- an organic EL display device using a TFT comprising, for example, amorphous silicone, micro crystal silicon, or an oxide semiconductor typified by In—Ga—Zn—O
- unfavorable phenomena such as a leak electric current or a photoinduced electric current
- a cured film obtainable from the resin composition of the present invention has a moderate absorption near 450 nm, the occurrence of a leak electric current, a photoinduced electric current, or the like is prevented and a stable driving/light emission characteristic is obtained by using for a dielectric layer, a planarization film, etc. in such an organic electroluminescence display device.
- a cured film to be obtained by curing the resin composition of the present invention can be used suitably for such applications as a surf ace protective film of a semiconductor element, such as LSI, an interlayer dielectric film, and an adhesive and an under fill agent for packing a device into a package, a capping agent that prevents copper migration, an on-chip microlens of a solid imaging element, and a planarization film for displays and solid imaging elements.
- a surf ace protective film of a semiconductor element such as LSI, an interlayer dielectric film, and an adhesive and an under fill agent for packing a device into a package
- a capping agent that prevents copper migration
- an on-chip microlens of a solid imaging element such as a planarization film for displays and solid imaging elements.
- a resin composition (hereinafter referred to as a varnish) was spin coated onto a 5 cm square glass substrate and was subjected to heat treatment (prebaking) at 120° C. for 2 minutes, so that a prebaked film having a thickness of 3.0 ⁇ m was produced.
- a varnish was spin coated so that its film thickness after curing might become 3.0 ⁇ m, and then heat treatment was carried out for 30 minutes at 230° C. under nitrogen flow (oxygen concentration 20 ppm or less) using an Inert Gas Oven INH-21CD available from Koyo Thermo Systems Co., Ltd., so that a cured film was produced.
- the varnishes prepared in Examples 4 to 11 and Comparative Examples 5 to 6 were each rotation coated onto a 6-inch silicon wafer and then heat-treated for 3 minutes on a hot plate (Mark-7), so that 4.0 ⁇ m thick prebaked films were produced.
- the prebaking temperature was adjusted to 120° C. for Examples 4 to 9 and Comparative Examples 5 to 6 and 100° C. for Examples 10 to 11.
- the resulting prebaked films were exposed with an exposure of 0 to 500 mJ/cm 2 at a 25 mJ/cm 2 step using an i-line stepper (DSW-8000, available from GCA).
- the line & space patterns used for the exposure are 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 50 and 100 ⁇ m.
- Example 10 to 11 heating was carried out at 100° C. for 1 minute after the exposure. After the exposure for Examples 4-9 or after the exposure and the following heating for Examples 10 to 11, development was performed in a 2.38 wt % aqueous solution of tetramethylammonium (TMAH) (ELM-D, available from Mitsubishi Gas Chemical Co., Inc.) for 60 seconds, followed by rinsing with pure water, so that developed films were obtained.
- TMAH tetramethylammonium
- ELM-D tetramethylammonium
- an exposure at which the exposed part was dissolved and disappeared through the development was defined as a photosensitivity.
- a negative type varnish the thickness of a film after development was measured and an exposure at which 90% of the thickness of a prebaked film remained was defined as a photosensitivity.
- the thickness after prebaking and that after development were measured using a Lambda Ace STM-602 available from Dainippon Screen Mfg. Co., Ltd. at an index of refraction of
- the resulting cured films were immersed in a stripping liquid 106 available from Tokyo Ohka Kogyo Co., Ltd. at 70° C. for 10 minutes.
- the thickness of a cured films before the stripping liquid treatment and the thickness of a cured film after that treatment were measured using a Lambda Ace STM-602 available from Dainippon Screen Mfg. Co., Ltd. at an index of refraction of 1.64, and then the reduction in film thickness was calculated.
- the reduction in film thickness is preferably 0.25 ⁇ m or less, more preferably 0.15 ⁇ m or less, and even more preferably 0.10 ⁇ m or less.
- Cured films were produced by the method described in the foregoing (i) using the varnishes prepared in Examples 4 to 11 and Comparative Examples 5 to 6.
- the resulting cured films were immersed in a stripping liquid 106 available from Tokyo Ohka Kogyo Co., Ltd. at 70° C. for 10 minutes.
- a cured film after the stripping liquid treatment was observed with an optical microscope of 20 magnifications, so that the presence of coming off of a pattern was evaluated. The smallest pattern having no coming off of a pattern was defined as being a remaining pattern.
- TrisP-PA commercial name, available from Honshu Chemical Industry Co., Ltd.
- NAC-5 5-naphthoquinonediazidosulfonyl chloride
- a triethylamine salt was filtered and the filtrate was poured into water. Then a precipitate formed was collected by filtration and washed with 1 L of 1% aqueous hydrochloric acid. Then it was further washed with 2 L of water twice. The precipitation was dried in a vacuum dryer, so that a quinone diazide compound represented by the following formula was obtained.
- a needlelike white crystal formed after being left at rest was collected by filtration and then was washed with 100 mL of water.
- the white crystal was vacuum dried at 50° C. for 48 hours.
- NMR GX-270, available from JEOL Ltd.
- DMSO-d6 a deuterated solvent
- a dry white crystal was obtained in the same manner as in Synthesis Example 3(1) except for using 169.6 g (0.4 mol) of 4,4′-[1-[4-[1-(4-hydroxyphenyl-1)-1-methylethyl]phenyl]ethylidene]bisphenol (TrisP-PA, available from Honshu Chemical Industry Co., Ltd.) instead of 103.2 g (0.4 mol) of 1,1,1-tris (4-hydroxyphenyl)ethane (TrisP-HAP, available from Honshu Chemical Industry Co., Ltd.).
- TrisP-PA 4,4′-[1-[4-[1-(4-hydroxyphenyl-1)-1-methylethyl]phenyl]ethylidene]bisphenol
- TrisP-PA 1,1,1-tris (4-hydroxyphenyl)ethane
- thermal cross-linking agents and acid generators used in the Examples and the Comparative Examples are as follows.
- a varnish of a polyimide resin composition was obtained in the same manner as in Example 1 except for adding 5 g of 2,6-dimethoxymethyl-t-butylphenol (available from Honshu Chemical Industry Co., Ltd.) instead of the alkoxymethyl group-containing compound (A-1) obtained in Synthesis Example 3.
- the transmittance at 450 nm of a film obtained using this varnish measured before or after curing was 96% and that after curing was 85%. This means that the change in transmittance was 11%.
- the chemical resistance of the cured film was evaluated, the film dissolved completely.
- THF tetrahydrofuran
- the solution was charged into 2 L of water and a precipitate of a polymer solid was collected by filtration. Furthermore, washing with 2 L of water was done three times and the collected polymer solid was dried at 50° C. in a vacuum dryer for 72 hours, so that an acrylic resin was obtained.
- the solution was charged into 2 L of water and a precipitate of a polymer solid was collected by filtration. Furthermore, washing with 2 L of water was done three times and the collected polymer solid was dried at 50° C. in a vacuum dryer for 72 hours, so that a polyamide acid was obtained.
- a varnish of a polyimide precursor composition was obtained by weighing 10 g of the thus obtained polyamide acid and dissolving 2 g of 1,6-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.) and 4 g of MW-30HM (available from Sanwa Chemical Co., Ltd.) in 20 g of EL and 20 g of GBL.
- the transmittance at 450 nm of a film obtained using this varnish measured before or after curing the transmittance before curing was 94% and that after curing was 40%. This means that the change in transmittance was 54%.
- the transmission spectra before and after curing are shown in FIG. 3 .
- the chemical resistance of the cured film was evaluated, the reduction in film thickness was 0.10 ⁇ m or less and therefore the chemical resistance was very good.
- a varnish of a polyimide resin composition was prepared in the same manner as in Example 2 except for adding 10 g of the polyimide powder obtained in Example 1 instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 95% and that after curing was 45%. This means that the change in transmittance was 50%. When the chemical resistance of the cured film was evaluated, the reduction in film thickness was 0.1 ⁇ m or less and therefore the chemical resistance was very good.
- a varnish of a novolac resin composition was prepared in the same manner as in Example 2 except for using 10 g of a novolac resin PSF2808 (available from Gun Ei Chemical Industry Co., Ltd.) instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 97% and that after curing was 88%. This means that the change in transmittance was 9%.
- the transmission spectra before and after curing are shown in FIG. 4 . The transmittance hardly dropped in the region of 400 nm or more after curing and therefore it was shown that coloring did not occurred in the visible range. When the chemical resistance of the cured film was evaluated, the film dissolved completely.
- a varnish of a polyhydroxystyrene resin composition was prepared in the same manner as in Example 2 except for using 10 g of a polyhydroxystyrene resin MARUKA LYNCUR S-2 (available from Maruzen Petrochemical Co., Ltd.) instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 97% and that after curing was 91%. This means that the change in transmittance was 6%.
- a varnish of a positive type photosensitive polyimide resin composition was obtained by further dissolving 4 g of the quinone diazide compound obtained in Synthesis Example 2 in the varnish of Example 1.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 95% before curing and 60% after curing. This means that the change in transmittance was 35%.
- the photosensitivity was 150 mJ/cm 2 .
- the reduction in film thickness was 0.10 ⁇ m or less. A pattern of 10 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was obtained by weighing 10 g of the polyamide acid obtained in Example 2 and dissolving 4 g of 1,7-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compound (A-2) obtained in Synthesis Example 4, and 4 g of the quinonediazide compound obtained in Synthesis Example 2 in 20 g of EL and 20 g of GBL.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 90% before curing and 59% after curing. This means that the change in transmittance was 31%.
- the photosensitivity was 150 mJ/cm 2 .
- the reduction in film thickness was 0.15 ⁇ m. A pattern of 10 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was prepared in the same manner as in Example 5 except for using 1-naphthol instead of 1,7-dihydroxynaphthalene and it was evaluated.
- the transmittance at 450 nm was 90% before curing and 77% after curing. This means that the change in transmittance was 13%.
- the reduction in film thickness was 0.20 ⁇ m.
- the photosensitivity was 300 mJ/cm 2 . A pattern of 20 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was prepared in the same manner as in Example 5 except for using 2,7-dihydroxynaphthalene instead of 1,7-dihydroxynaphthalene and it was evaluated.
- the transmittance at 450 nm was 90% before curing and 74% after curing. This means that the change in transmittance was 16%.
- the reduction in film thickness was 0.15 ⁇ m.
- the photosensitivity was 150 mJ/cm 2 . A pattern of 10 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was prepared by further dissolving, in the varnish of Example 5, 0.5 g of 5-propylsulfonyloxyimino-5H-thiophene-2-methylphenyl-acetonitrile (commercial name PAG-103, available from Ciba Specialty Chemicals Corporation) as a thermal acid generator.
- PAG-103 5-propylsulfonyloxyimino-5H-thiophene-2-methylphenyl-acetonitrile
- the transmittance at 450 nm was 90% before curing and 59% after curing. This means that the decrease in transmittance was 31%.
- the photosensitivity was 150 mJ/cm 2 .
- the reduction in film thickness was 0.10 ⁇ m or less. A pattern of 10 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was obtained by further dissolving, in the varnish of Example 5, 0.5 g of the adhesion promoter (B-1) obtained in Synthesis Example 6.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 90% before curing and 59% after curing. This means that the change in transmittance was 31%.
- the photosensitivity was 150 mJ/cm 2 .
- the reduction in film thickness was 0.15 ⁇ m. A pattern of 3 ⁇ m or more remained.
- a varnish of a positive type photosensitive polyimide precursor composition was obtained by weighing 10 g of the polyamide acid obtained in Example 2 and dissolving 4 g of 2,3-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compound (A-2) obtained in Synthesis Example 4, and 4 g of the quinonediazide compound obtained in Synthesis Example 2 in 20 g of EL and 20 g of GBL.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 93% before curing and 63% after curing. This means that the change in transmittance was 30%.
- the reduction in film thickness was 0.15 ⁇ m.
- the photosensitivity was 200 mJ/cm 2 . A pattern of 10 ⁇ m or more remained.
- a varnish of a positive type photosensitive polybenzoxazole precursor composition was obtained by dissolving 10 g of the obtained polyhydroxyamide, 4 g of 1,5-dihydroxynaphthalene, 2 g of the quinone diazide compound of Synthesis Example 2, 0.5 g of WPAG-314 (commercial name, available from Wako Pure Chemical Industries, Ltd.), and 5 g of MX-270 in 10 g of EL and 30 g of GBL.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 92% before curing and 61% after curing. This means that the decrease in transmittance was 31%.
- the reduction in film thickness was 0.25 ⁇ m and the photosensitivity was 160 mJ/cm 2 .
- a varnish of a negative type photosensitive polybenzoxazole precursor composition was obtained by dissolving 10 g of the polyhydroxyamide obtained in Example 9, 1.5 g of 1,7-dihydroxynaphthalene, 0.5 g of WPAG-314 (commercial name, available from Wako Pure Chemical Industries, Ltd.), 0.5 g of 5-propylsulfonyloxyimino-5H-thiophene-2-methylphenyl-acetonitrile (commercial name PAG-103, available from Ciba Specialty Chemicals Corporation) as a thermal acid generator, and 2 g of MW-30HM in 40 g of GBL.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 95% before curing and 57% after curing. This means that the change in transmittance was 38%.
- the reduction in film thickness was 0.25 ⁇ m and the photosensitivity was 200 mJ/cm 2 . A pattern of 20 ⁇ m or more remained.
- a varnish of a negative type photosensitive polyimide resin composition was obtained by adding 5 g of 1,7-dihydroxynaphthalene, 4 g of the alkoxymethyl group-containing compounds (A-3) obtained in Synthesis Example 5, 2 g of ethyleneoxide-modified bisphenol A dimethacrylate (NK ester BPE-100, available from Shin-Nakamura Chemical Co., Ltd.), 0.5 g of trimethylolpropane triacrylate, 0.1 g of 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyloxime)](available from Ciba Specialty Chemicals Corporation), 20 g of EL, and 20 g of GBL to 10 g of the polyimide obtained in Example 1.
- the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above.
- the transmittance at 450 nm was 94% before curing and 66% after curing. This means that the change in transmittance was 28%.
- the reduction in film thickness was 0.1 ⁇ m and the photosensitivity was 200 mJ/cm 2 . A pattern of 10 ⁇ m or more remained.
- a bottom gate type TFT was formed on a glass substrate and wiring (1.0 ⁇ m in height) connected to the TFT was formed.
- a dielectric film made of Si 3 N 4 was formed so that the TFT and the wires might be covered therewith. Next, a contact hole was formed in this dielectric film.
- a planarization film was formed on the dielectric film in order to planarize the irregularities of the TFT and the wires.
- the formation of the planarization film on the dielectric film was carried out by spin coating the varnish of the photosensitive polyimide precursor composition obtained in Example 5 onto the substrate, prebaking it on a hot plate at 120° C. for 3 minutes, then exposing and developing it, and then subjecting it to heat calcination at 250° C. for 60 minutes under air flow.
- the coating property at the time of coating the varnish was good and no development of wrinkles or cracks was found in the cured film obtained after the exposure, development and calcination.
- the average step height of the wires was 500 nm and the thickness of the produced planarization film was 2000 nm.
- a top emission type organic EL element was formed on the resulting planarization film.
- a bottom electrode of ITO was formed on the planarization film by sputtering in connection with a wire via a contact hole. Then, a resist was coated, prebaked, and exposed through a mask of a desired pattern, thereby being developed. Pattern processing was carried out by wet etching using an ITO etchant and using the resist pattern as a mask. Then, the resist pattern was stripped using a resist stripping liquid (a mixed liquid of monoethanolamine and DMSO). The thus obtained bottom electrode corresponds to an anode of an organic EL element.
- a resist stripping liquid a mixed liquid of monoethanolamine and DMSO
- a dielectric layer shaped so that it might cover the bottom electrode was formed.
- the varnish of the photosensitive polyimide precursor composition obtained in Example 5. By providing this dielectric layer it is possible to prevent short-circuit between the bottom electrode and an upper electrode to be formed in a subsequent step.
- the dielectric layer was patterned and was subjected to heating treatment at 250° C. for 60 minutes, so that a dielectric layer having a moderate absorption near a wavelength of 450 nm was formed.
- a hole transporting layer, red, green, and blue organic light-emitting layers, and an electron transporting layer were provided one after another by vapor deposition via a desired pattern mask in a vacuum deposition apparatus.
- an upper electrode of aluminum was formed over the whole top surface of the substrate. This corresponds to a cathode of an organic EL element.
- the aforementioned substrate obtained was taken out of the vacuum deposition apparatus and then was sealed by bonding it to a sealing glass substrate using an ultraviolet-curable epoxy resin.
- a bottom gate type TFT was formed on a glass substrate and wiring (1.0 ⁇ m in height) connected to the TFT was formed.
- a dielectric film made of Si 3 N 4 was formed so that the TFT and the wires might be covered therewith. Next, a contact hole was formed in this dielectric film.
- This wiring is an item for connecting a TFT and another TFT or an organic EL element to be formed in a subsequent step and a TFT.
- a bottom electrode of ITO was formed by sputtering in connection with a wire via a contact hole. Then, a resist was coated, prebaked, and exposed through a mask of a desired pattern, thereby being developed. Pattern processing was carried out by wet etching using an ITO etchant and using the resist pattern as a mask. Then, the resist pattern was stripped using a resist stripping liquid (a mixed liquid of monoethanolamine and DMSO). The thus obtained bottom electrode corresponds to an anode of an organic EL element.
- a resist stripping liquid a mixed liquid of monoethanolamine and DMSO
- a dielectric layer having such a shape that it could cover the periphery of the bottom electrode, the TFT, and the steps of the wires was formed.
- the varnish of the photosensitive polyimide precursor composition obtained in Example 5 was spin coated onto the substrate, subsequently dried under reduced pressure, then prebaked on a hot plate at 120° C. for 3 minutes, then exposed and developed, and then subjected to heat calcination at 250° C. for 60 minutes under nitrogen flow.
- the coating property at the time of spin coating the varnish was good and no development of wrinkles or cracks was found in the cured film obtained after the exposure, development and calcination.
- the average step height of the wires was 500 nm and the thickness of the produced dielectric layer was 2000 nm.
- a hole transporting layer, red, green, and blue organic light-emitting layers, and an electron transporting layer were provided one after another by vapor deposition via a desired pattern mask in a vacuum deposition apparatus.
- an upper electrode of aluminum was formed over the whole top surface of the substrate. This corresponds to a cathode of an organic EL element.
- the aforementioned substrate obtained was taken out of the vacuum deposition apparatus and then was sealed by bonding it to a sealing glass substrate using an ultraviolet-curable epoxy resin.
- the resin composition of the present invention can be used suitably for applications such as a surface protective film and an interlayer dielectric film of a semiconductor element, a dielectric layer of an organic EL element, a planarization film of a TFT substrate for driving of a display device using an organic EL element, a wire-protecting dielectric film of a circuit board, an on-chip microlens of a solid imaging element, a planarization film for displays and solid imaging elements, a solder resist for circuit boards, an underfill agent, and a capping agent for preventing copper migration.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- The present application is a 37 C.F.R. §1.53 (b) divisional of, and claims priority to, U.S. application Ser. No. 13/146,794, filed Aug. 9, 2011. application Ser. No. 13/146,794 is the national phase under 35 U.S.C. §371 of International Application No. PCT/JP2010/050402, filed on Jan. 15, 2010, which claims priority to Japanese Application No. 2009-017790 filed on Jan. 29, 2009. The entire contents of each of these applications is hereby incorporated by reference.
- The present invention relates to resin compositions. Particularly, it relates to resin compositions suited for applications such as surface protective films and interlayer dielectric films of semiconductor elements, dielectric layers of organic electroluminescent (hereinafter referred to as EL) elements, planarization films of thin film transistor (hereinafter referred to as TFT) substrates for the driving of display devices using organic EL elements, wire-protecting dielectric films of circuit boards, on-chip microlens of solid imaging elements, planarization films for displays and solid imaging elements, and solder resists for circuit boards.
- Cured films produced by curing compositions containing polyimide or polybenzoxazole have been used widely for dielectric films, protective films, planarization films, and the like of semiconductor elements or display devices. Particularly in display devices, it is required to reduce the transmittance of a cured film in order to increase contrast in applications such as, for example, a dielectric layer of an organic EL display and a black matrix of a liquid crystal display. In order to prevent malfunction caused by penetration of light into a TFT for driving of a display device, a leak electric current, and the like, it is required to reduce the transmittance of a dielectric layer of an organic EL device or a planarization film to be provided on a TFT substrate of an organic EL display. Examples of a technology of reducing the transmittance of a visible region greater than a wavelength of 400 nm in a cured film include a method of adding a colorant, such as carbon black, an organic or inorganic pigment, and a dyestuff, to a resin composition like that seen in a black matrix material for liquid crystal displays, an RGB paste material, and the like. Since resin compositions containing such colorants have absorption in a exposure wavelength region of 400 to 450 nm, it is difficult to use them as positive type photosensitive resin compositions which are sensitized by making light reach to a film bottom and therefore the use as a negative type photosensitive resin composition such that a film thereof is photocured from its surface is common.
- Examples of a technology of reducing the transmittance of a cured film of a positive type photosensitive resin composition include a positive type radiative resin composition comprising an alkali-soluble resin, a quinone diazide compound, and a coloring composition of a leuco dye, a developing agent, and so on (see, for example, patent document 1), a photosensitive resin in which a heat-sensitive material that will become black upon heating has been added beforehand (see, for example, patent document 2), and a positive type photosensitive resin composition comprising an alkali-soluble resin, a quinone diazide compound, a thermally coloring compound that colors upon heating and exhibits an absorbance maximum at 350 nm or more and 700 nm or less, and a compound that has no absorbance maximum at 350 nm or more and less than 500 nm and has an absorbance maximum at 500 nm or more and 750 nm or less (see, for example, patent document 3). These are technologies of reducing the transmittance of a cured film while keeping the transmittance in the exposure wavelength region of the resin film before curing high by using a coloring compound that colors due to energy, such as heat. Therefore, these can impart both positive photosensitivity and negative photosensitivity to resin compositions with high versatility.
-
- [Patent Document 1] JP 2008-122501 A
- [Patent Document 2] JP 10-170715 A
- [Patent Document 3] US Patent Application Publication No. 2004/197703 Specification
- Coloring compounds are compounds that will have intramolecular structural change themselves due to heat to develop absorption in a specified wavelength region. Recently, not only coloring compounds but also resin compositions capable of developing absorption in an exposure wavelength region by other means have been demanded in order to improve versatility. Then, an object of the present invention is to provide a resin composition that can reduce the transmittance in the visible region of a cured film by the use of a combination of specific compounds while maintaining the transmittance of the resin film before curing.
- That is, the present invention provides a resin composition comprising (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, and (c) a thermal cross-linking agent having a structure represented by the following formula (1) or a thermal cross-linking agent having a group represented by the following formula (2):
- [kagaku 1]
- in formula (1), R represents a linking group having 2 to 4 valencies, R1 represents a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F, R2 and R3 each represent CH2OR5 (R5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms), R4 represents a hydrogen atom, a methyl group or an ethyl group, s represents an integer of 0 to 2 and u represents an integer of 2 to 4;
-
—N(CH2OR6)t(H)v (2) - wherein in formula (2), R6 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, t is 1 or 2 and v is 0 or 1, provided that t+v is 1 or 2.
- According to the present invention, it is possible to obtain a resin composition that can reduce the transmittance in the visible region of a cured film while maintaining the transmittance of the resin film before curing.
-
FIG. 1 is a sectional view of a TFT substrate in which a planarization film and a dielectric layer have been formed. -
FIG. 2 is a sectional view of a TFT substrate in which a dielectric layer has been formed. -
FIG. 3 is a transmission spectra of the resin composition of Example 2 before and after curing. -
FIG. 4 is a transmission spectra of the resin composition of Comparative Example 3 before and after curing. - The resin composition of the present invention comprises (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, and (c) a thermal cross-linking agent having a structure represented by the formula (1) provided above or a thermal cross-linking agent having a group represented by the formula (2) provided above. The combination of component (b) and component (c) with the resin of component (a) makes it possible to make a cured film color at 400 to 450 nm to reduce the transmittance in the visible range greatly. Lack of any one of the three compounds (a) to (c) will result in difficulty in the intended coloring at 400 450 nm. The components will be described below.
- The resin composition of the present invention includes (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor. It may include two or more of them and also may include a copolymer that has two or more of their repeating units.
- Polyimide and polybenzoxazole are resins that have a cyclic structure of an imide ring or an oxazole ring in their main chain. The number of repetitions of the repeating units is preferably 10 to 100000.
- Polyimide can be obtained by reacting a tetracarboxylic acid or its corresponding tetracarboxylic dianhydride or corresponding tetracarboxylic acid diester dichloride with a diamine or its corresponding diisocyanate compound or corresponding trimethylsilylated diamine and it has a tetracarboxylic acid residue and a diamine residue. For example, it can be obtained by dehydration-cyclizing a polyamide acid, which is one of the polyimide precursors produced by making a tetracarboxylic dianhydride react with a diamine, by heating treatment or chemical treatment. In the heating treatment, a solvent that azeotropically boils with water, such as m-xylene, may be added. The heating treatment may be done at a low temperature of equal to or lower than 100° C. with the addition of a weakly acidic carboxylic acid compound. Examples of the cyclization catalyst to be used for the chemical treatment include dehydration condensation agents such as carboxylic anhydrides and dicyclohexyl carbodiimide and bases such as triethylamine. A description of the polyimide precursor will be made later.
- Polybenzoxazole can be obtained by making a bisaminophenol compound react with a dicarboxylic acid, its corresponding dicarboxylic acid chloride or corresponding dicarboxylic acid active ester and it has a dicarboxylic acid residue and a bisaminophenol residue. For example, it can be obtained by dehydration-cyclizing a polyhydroxyamide, which is one of the polybenzoxazole precursors produced by making a bisaminophenol compound react with a dicarboxylic acid react, by heating treatment or chemical treatment. In the heating treatment, a solvent that azeotropically boils with water, such as m-xylene, may be added. Moreover, the heating treatment may be done at a low temperature of equal to or lower than 200° C. with the addition of an acidic compound. Examples of the cyclization catalyst to be used for the chemical treatment include phosphoric anhydride, bases, and carbodiimide compounds. A description of the polybenzoxazol precursor will be made later.
- In the present invention, from the viewpoint of solubility in an aqueous alkali solution, the polyimide preferably has an acidic group or an acidic group derivative such as OR7, SO3R7, CONR7R8, COOR7, and SO2NR7R8, in a tetracarboxylic acid residue or a diamine residue, and it more preferably has a hydroxyl group. In addition, the polybenzoxazole preferably has an acidic group or an acidic group derivative, such as OR7, SO3R7, CONR7R8, COOR7, and SO2NR7R8, in a dicarboxylic acid residue or a bisaminophenol residue, and it more preferably has a hydroxyl group. R7 and R8 each represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. The acidic group refers to a case where all of R7 or R8 are hydrogen atoms, and the acidic group derivative refers to a case where a monovalent organic group having 1 to 20 carbon atoms is contained in R7 or R8.
- In the present invention, examples of preferred structures of a tetracarboxylic acid residue of a polyimide and a dicarboxylic acid residue of a polybenzoxazole (these are hereinafter referred to as an acid residue) include structures provided below or structures resulting from replacing 1 to 4 hydrogen atoms of those structures by an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, a fluorine atom, or a chlorine atom. Two or more of these may be used together.
- [kagaku 2]
- [kagaku 3]
- It is noted that J represents a direct bond, —COO—, —CONH—, —CH2—, and —C2H4—, —O—, —C3H6—, —SO2—, —S—, —Si(CH3)2—, —O—Si(CH3)2—O—, —C6H4—, —C6H4—O—C6H4—, —C6H4—C3H6—C6H4—, or —C6H4—C3F6—C6H4—.
- In the present invention, examples of preferred structures of a diamine residue of a polyimide and a bisaminophenol residue of a polybenzoxazole (these are hereinafter referred to as an amine residue) include structures provided below or structures resulting from replacing 1 to 4 hydrogen atoms of those structures by an alkyl group having 1 to 20 carbon atoms, a fluoroalkyl group, an alkoxyl group, an ester group, a nitro group, a cyano group, a fluorine atom, or a chlorine atom. Two or more of these may be used together.
- [kagaku 4]
- [kagaku 5]
- It is noted that J represents a direct bond, —COO—, —CONH—, —CH2—, —C2H4—, —O—, —C3H6—, —SO2—, —S—, —Si (CH3)2—, —O—Si (CH3)2—O—, —C6H4—, —C6H4—O—C6H4—, —C6H4—C3H6—C6H4—, or —C6H4—C3F6—C6H4—. R7 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
- Of the component (a) to be used for the present invention, the polyimide precursor and the polybenzoxazole precursor are resins that have an amide bond in their main chain and are dehydration-cyclized by heating treatment or chemical treatment to become the aforementioned polyimide and polybenzoxazole. The number of repetitions of the repeating units is preferably 10 to 100000. Examples of the polyimide precursor include a polyamide acid, a polyamide acid ester, a polyamide acid amide, and a polyisoimide, and a polyamide acid and a polyamide acid ester are preferred. Examples of the polybenzoxazole precursor include a polyhydroxyamide, a polyaminoamide, polyamide, and a polyamide-imide, and a polyhydroxyamide is preferred. In the present invention, from the viewpoint of solubility in an aqueous alkali solution, the polyimide precursor and the polybenzoxazole precursor preferably have an acidic group or an acidic group derivative such as OR7, SO3R7, CONR7R8, COOR7, and SO2NR7R8, in an acid residue or an amine residue, and they more preferably have a hydroxyl group. R7 and R8 represent hydrogen atoms or monovalent organic groups having 1 to 20 carbon atoms. The acidic group refers to a case where all of R7 or R8 are hydrogen atoms, and the acidic group derivative refers to a case where a monovalent organic group having 1 to 20 carbon atoms is contained in R7 or R8.
- Regarding the acid component that constitutes the acid residue of the polyimide precursor and the polybenzoxazole precursor, examples of a dicarboxylic acid include terephthalic acid, isophthalic acid, diphenylether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenone dicarboxylic acid, and triphenyldicarboxylic acid. Example of a tricarboxylic acid include trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid. Examples of a tetracarboxylic acid include aromatic tetracarboxylic acids, such as pyromellitic acid, 3,3′,4,4′-biphenyl tetracarboxylic acid, 2,3,3′,4′-biphenyl tetracarboxylic acid, 2,2′,3,3′-biphenyl tetracarboxylic acid, 3,3′,4,4′-benzophenonetetracarboxylic acid, 2,2′,3,3′-benzophenone tetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane, bis(2,3-dicarboxyphenyl)methane, bis(3,4-dicarboxyphenyl)sulfone, bis(3,4-dicarboxyphenyl)ether, 1,2,5,6-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 2,3,5,6-pyridinetetracarboxylic acid and 3,4,9,10-perylene tetracarboxylic acid, and aliphatic tetracarboxylic acids, such as butanetetracarboxylic acid, a cyclobutanetetracarboxylic acid, 1,2,3,4-cyclopentanetetracarboxylic acid, cyclohexanetetracarboxylic acid, bicyclo[2.2.1.]heptanetetracarboxylic acid, bicyclo[3.3.1.]tetracarboxylic acid, bicyclo[3.1.1.]hept-2-ene tetracarboxylic acid, bicyclo[2.2.2.]octane tetracarboxylic acid, and adamantane tetracarboxylic acid. Two or more of these may be used together. More preferred are the dicarboxylic acids, tricarboxylic acids or tetracarboxylic acids provided above as examples whose 1 to 4 hydrogen atoms have been substituted with an acidic group or acidic group derivative, such as OR7, SO3R7, CONR7R8, COOR7, and SO2NR7R8, preferably with a hydroxyl group, a sulfonic acid group, a sulfonic acid amide group, or a sulfonic acid ester group.
- These acids each can be used as it is or in the form of an acid anhydride or an active ester.
- By the use of a silicon atom-containing tetracarboxylic acid such as dimethylsilanediphthalic acid and 1,3-bis(phthalic acid)tetramethyldisiloxane, it is possible to enhance the adhesion property to a substrate and the resistance to oxygen plasma to be used for washing and resistance to a UV ozone treatment. These silicon atom-containing tetracarboxylic acids are preferably used in 1 to 30 mol % of the whole acid component.
- Examples of the diamine component that constitutes the amine residue of the polyimide precursor and the polybenzoxazole precursor include hydroxyl group-containing diamines, such as bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, bis(3-amino-4-hydroxy)biphenyl, bis(3-amino-4-hydroxyphenyl)fluorene, carboxyl group-containing diamines, such as 3,5-diaminobenzoic acid and 3-carboxy-4,4′-diaminodiphenyl ether, sulfonic acid-containing diamines, such as 3-sulfonic acid-4,4-diaminodiphenyl ether, dithiohydroxyphenylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 3,4′-diaminodiphenyl sulfone, 4,4′-diaminodiphenyl sulfone, 3,4′-diaminodiphenylsulfide, 4,4′-diaminodiphenylsulfide, 1,4-bis(4-aminophenoxy)benzene, benzine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl}ether, 1,4-bis(4-aminophenoxy)benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, 3,3′-dimethyl-4,4′-diaminobiphenyl, 3,3′-diethyl-4,4′-diaminobiphenyl, 2,2′,3,3′-tetramethyl-4,4′-diaminobiphenyl, 3,3′,4,4′-tetramethyl-4,4′-diaminobiphenyl, 2,2′-di(trifluoromethyl)-4,4′-diaminobiphenyl, or compounds each resulting from replacing some halogen atoms of the aromatic ring of each of the foregoing by an alkyl group or a halogen atom, aliphatic diamines, such as cyclohexyldiamine and methylenebiscyclohexylamine. Furthermore, these diamines may be substituted with an alkyl group having 1 to 10 carbon atoms, such as a methyl group and an ethyl group, a fluoroalkyl group having 1 to 10 carbon atoms, such as a trifluoromethyl group, or a group such as F, Cl, Br, and I. Two or more of these may be used together. For an application in which heat resistance is required, it is preferred to use an aromatic diamine in 50 mol % or more of the whole diamine. In addition, the diamines provided above as examples preferably have an acidic group or an acidic group derivative, such as OR7, SO3R7, CONR7R8, COOR7, and SO2NR7R8, and they more preferably have a hydroxyl group.
- These diamines can be used as they are or in the form of a corresponding diisocyanate compound or trimethylsilylated diamine.
- The use of a silicon atom-containing diamine, such as 1,3-bis(3-aminopropyl)tetramethyldisiloxane and 1,3-bis(4-anilino)tetramethyldisiloxane, as a diamine component can enhance adhesion property to a substrate or resistance to oxygen plasma to be used for washing and resistance to a UV ozone treatment. These silicon atom-containing diamines are preferably used in 1 to 30 mol % of the whole diamine component.
- It is preferred to cap the end of a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor with a monoamine having a hydroxyl group, a carboxyl group, a sulfonic acid group, or a thiol group, an acid anhydride, an acid chloride, or a monocarboxylic acid. Two or more of these may be used together. The dissolution rate of a resin to an aqueous alkali solution can be adjusted easily to a preferable range by the possession of the aforementioned group at a resin end.
- Preferable examples of a monoamine include 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminothiophenol, 3-aminothiophenol, and 4-aminothiophenol.
- Preferable examples of the acid anhydride, the monoacid chloride, the monocarboxylic acid, and the mono-active ester compound include acid anhydrides, such as phthalic anhydride, maleic anhydride, nasic acid, cyclohexane dicarboxylic acid anhydride, and 3-hydroxyphthalic acid anhydride; monocarboxylic acids, such as 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, and 4-carboxybenzenesulfonic acid, and monoacid chloride compounds resulting from conversion of their carboxyl groups to acid chlorides; monoacid chloride compounds resulting from conversion of one carboxyl group of a dicarboxylic acid, such as terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, and 2,6-dicarboxynaphthalene, into an acid chloride; and mono-active ester compounds obtained through a reaction between a monoacid chloride compound and N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboxylmide.
- The content of the end-capping agent, such as the aforementioned monoamine, acid anhydride, acid chloride, and monocarboxylic acid, is preferably within a range of 0.1 to 60 mol %, more preferably from 5 to 50 mol %, of the number of moles of the charged acid component monomer to constitute an acid residue or the charged diamine component monomer to constitute an diamine residue. By adjusting the content to such a range, a resin composition that is moderate in viscosity of its solution when applying the resin composition and that has superior film properties can be obtained.
- The resin also may have a polymerizable functional group at its end. Examples of the polymerizable functional group include an ethylenically unsaturated linking group, anacetylene group, a methylol group, and an alkoxymethyl group.
- The end-capping agent having been introduced into a resin can be detected easily by the following method. For example, an end-capping agent can be detected easily by dissolving a resin into which the end-capping agent has been introduced in an acidic solution to decompose the resin into an amine component and an acid component which are constitutional units of the resin, and then measuring them by gas chromatography (GC) or NMR. Aside from this, a resin in which an end-capping agent has been introduced can be detected directly through the measurement of a pyrolysis gas chromatograph (PGC), an infrared spectrum, and 13C-NMR.
- In the present invention, a polyimide precursor or a polybenzoxazole precursor is preferred as component (a) and a polyimide precursor is more preferred. A polyimide precursor advances an imidation reaction in which an amide acid moiety is cyclized by curing calcination at about 200° C., and a polybenzoxazole precursor advances an oxazolation reaction in which a hydroxyamide moiety is cyclized by curing calcination at about 300° C., resulting in remarkable improvement in chemical resistance. The polyimide precursor makes it possible to obtaine chemical resistance at a lower calcination temperature. A photosensitive resin composition using such a precursor resin having a property to volumetrically shrink at the time of curing calcination makes it possible to obtain a pattern in a forward-tapered form by obtaining a fine pattern by an exposure-development step and then performing calcination. This pattern in a forward-tapered form is superior in ability to cover an upper electrode when being used as a dielectric film of an organic EL element, and it can prevent breakage of wiring and can improve the reliability of an element.
- The resin composition of the present invention may contain alkali-soluble resins other than component (a). An alkali-soluble resin refers to any resin having an acidic group to become soluble in alkali and specific examples thereof include radically polymerizable polymers having acrylic acid, a phenol novolak resin, and polyhydroxystyrene, polysiloxane. It is also permitted to adjust the alkali solubility by protecting the acidic groups of these resins. Such a resin is a substance that is soluble in an aqueous solution of an alkali, such as choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate as well as tetramethylammonium hydroxide. Although two or more such resins may be contained, their proportion to the whole resin including component (a) is preferably up to 50% by weight.
- The resin composition of the present invention contains (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene. Two or more of these may be contained. The possession of two hydroxyl groups results in better alkali developability in comparison to a case of possessing one hydroxyl group and can improve photosensitivity. The naphthalene structure, which is a fused polycyclic structure, is higher in electron density than a monocyclic compound and it comes to have an increased electron density through its possession of two hydrogen groups and can effectively cause an electrophilic addition reaction of a thermal cross-linking agent (c) described later. Moreover, the conjugation of n-electrons is prone to spread in two or more directions to develop color after the formation of a cross-linking reaction, and therefore, it is possible to greatly reduce the transmittance in the visible region of a cured film by combining it with a thermal cross-linking agent (c) described later. Such an effect becomes particularly remarkable when the structure has hydroxyl groups at 1,5-positions, 1,6-positions, 1,7-positions, or 2,3-positions. Moreover, by a cross-linking reaction of the thermal cross-linking agent (c) and the above-mentioned component (a), it is possible to fix the compound of component (b) to component (a), which is superior in heat resistance, so that the chemical resistance of a cured film can be improved.
- The resin composition of the present invention may contain, in addition to (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, another fused polycyclic aromatic compound having two or more hydroxyl groups.
- Examples of the skeleton structure of the fused polycyclic aromatic compound having two or more hydroxyl groups include carbon fused bicyclic structure, such as pentalene, indene, naphthalene, azulene, heptalene, and octalene, carbon fused tricyclic structure, such as as-indacene, s-indacene, biphenylene, acenaphthylene, fluorene, phenanthrene, and anthracene, carbon fused tetracyclic structure, such as trindene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, tetraphene, and naphthacene, and carbon fused pentacyclic structure, such as picene, perylene, pentaphene, pentacene, and tetraphenylene. A heterocyclic structure containing nitrogen, sulfur, or oxygen atoms instead of some carbon atoms of the aforementioned carbon fused polycyclic aromatic compounds is also available. Examples of the fused polycyclic aromatic heterocompound include fused heterobicyclic compounds, such as benzofuran, benzothiophene, indole, benzimidazole, benzothiazole, purine, quinoline, isoquinoline, cinnoline, and quinoxaline, and fused heterotricyclic compounds, such as dibenzofuran, carbazole, acridine, and 1,10-phenanthroline. Compounds each resulting from replacing some hydrogen atoms of a compound having a skeleton provided above as an example by two or more hydroxyl groups are preferred as the fused polycyclic aromatic compound having two or more hydroxyl groups.
- Specific examples of the fused polycyclic aromatic compound having two or more hydroxyl groups include 1,4-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,4-dihydroxyquinoline, 2,6-dihydroxyquinoline, 2,3-dihydroxyquinoxaline, anthracene-1,2,10-triol, and anthracene-1,8,9-triol.
- In the resin composition of the present invention, the content of (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, or 1,7-dihydroxynaphthalene is preferably 5 parts by weight or more, more preferably 10 parts by weight or more relative to 100 parts by weight of the resin of component (a). It is preferably 120 parts by weight or less, and more preferably 100 parts by weight or less. If the content of component (b) is 5 parts by weight or more, the transmittance in the visible region of a cured film can be reduced more. If it is 120 parts by weight or less, it is possible to maintain the strength of a cured film and reduce the percentage of water absorption. When containing two or more kinds of component (a) or component (b), their total amount is preferably within the above-mentioned range.
- The resin composition of the present invention contains (c) a thermal cross-linking agent having a structure represented by the following formula (1) or a thermal cross-linking agent having a group represented by the following formula (2). Two or more of these may be contained. The thermal cross-linking agent of component (c) can reduce the transmittance of the visible range greatly by cross-linking itself to both (a) a polyimide, a polybenzoxazole, a polyimide precursor, or a polybenzoxazole precursor, and (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, thereby linking the three components (a), (b), and (c) together. Moreover, it can increase the chemical resistance of a cured film through a cross-linking reaction.
- [kagaku 6]
- In formula (1), R represents a linking group having 2 to 4 valencies. R1 represents a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F. Monovalent hydrocarbon groups having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group, are preferred as the monovalent organic group having 1 to 20 carbon atoms. R2 and R3 each represent CH2OR5 (R5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms). R4 represents a hydrogen atom, a methyl group or an ethyl group. s represents an integer of 0 to 2 and u represents an integer of 2 to 4. A plurality of R1s is to R4s each may be the same or different. Examples of the linking group R are provided below.
- [kagaku 7]
- In the above formula, R9 to R27 each represent a hydrogen group, a monovalent organic group having 1 to 20 carbon atoms, Cl, Br, I, or F. A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, a cyclohexyl group, a benzyl group, and a naphthyl group are preferred as the monovalent organic group having 1 to 20 carbon atoms.
-
—N(CH2OR6)t(H)v (2) - In the above formula (2), R6 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms. t represents 1 or 2 and v represents 0 or 1, provided that t+v is 1 or 2.
- In the above formula (1), R2 and R3 each represent a thermally cross-linkable group, CH2OR5 (R5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms). R5 is preferably a monovalent hydrocarbon group having 1 to 4 carbon atoms because it leaves a moderate reactivity and excels in storage stability. In a photosensitive resin composition containing a photo acid generator, a photopolymerization initiator, or the like, R5 is more preferably a methyl group or an ethyl group.
- In the thermal cross-linking agent represented by formula (1), the number of the functional groups of the thermally cross-linkable groups accounting for in one molecule is 4 to 8. If the number of the functional groups is less than 4, it is impossible to color the resin composition after curing moderately and also impossible to reduce the transmittance in the visible region of a cured film. On the other hand, if the number of the functional groups exceeds 8, it is difficult to obtain a compound that is high in purity and the stability of the compound itself and the storage stability in a resin composition deteriorate.
- The purity of the compound having a structure represented by formula (1) is preferably 75% or more, and more preferably 85% or more. If the purity is 85% or more, the storage stability is good, a cross-linking reaction of a resin composition is fully carried out, resulting in a superior coloring property after curing, and it is possible to reduce the transmittance in the visible region of a cured film. Since it is possible to reduce unreacted groups, that serve as water-absorptive groups, it is possible to reduce the water absorptivity of a resin composition. Examples of the method for obtaining a thermal cross-linking agent having a high purity include recrystallization and distillation. The purity of the thermal cross-linking agent can be determined by liquid chromatography.
- Preferable examples of the thermal cross-linking agent having a structure represented by formula (1) are given below.
- [kagaku 8]
- [kagaku 9]
- In formula (2), R6, which is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, preferably is a monovalent hydrocarbon group having 1 to 4 carbon atoms. From the viewpoint of the stability of a compound or the storage stability in a resin composition, it is preferred, in a photosensitive resin composition containing a photo acid generator, a photopolymerization initiator, or the like, that R6 be a methyl group or an ethyl group and it is preferred that the number of the (CH2OR6) groups contained in the compound be 8 or less.
- Preferable examples of the thermal cross-linking agent having a group represented by formula (2) are given below.
- [kagaku 10]
- The content of (c) the thermal cross-linking agent having a structure represented by formula (1) or the thermal cross-linking agent having a group represented by formula (2) is preferably 5 parts by weight or more and more preferably is 10 parts by weight or more relative to 100 parts by weight of the resin of component (a). It is preferably 120 parts by weight or less, and more preferably 100 parts by weight or less. If the content of component (c) is 5 parts by weight or more, the transmittance in the visible region of a cured film can be reduced more. If it is 120 parts by weight or less, the strength of a cured film is high and also the resin composition is superior in storage stability. When containing two or more kinds of component (a) or component (c), their total amount is preferably within the above-mentioned range.
- The resin composition of the present invention may further comprise (d) a photo acid generator, or (e) a photopolymerization initiator and (f) a compound having two or more ethylenically unsaturated bonds and can impart positive type or negative type photosensitivity.
- Due to the inclusion of (d) the photo acid generator in the resin composition of the present invention, an acid is generated by in a part exposed to light, so that the solubility of a part exposed to light in an aqueous alkali solution increases and a positive type relief pattern in which the part exposed to light dissolves can be obtained. Moreover, the inclusion of (d) the photo acid generator and an epoxy compound makes it possible to obtain a negative type relief pattern in which acids generated in a part exposed to light promotes the reaction of the epoxy compound, so that the part exposed to light becomes insoluble.
- Examples of (d) the photo acid generator include quinone diazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts.
- Examples of the quinone diazide compound include a compound in which the sulfonic acid of quinone diazide has been bonded to a polyhydroxy compound via an ester, a compound in which the sulfonic acid of quinone diazide has been sulfonamide-bonded to a polyamino compound, and a compound in which the sulfonic acid of quinone diazide has been ester-bonded and/or sulfonamide-bonded to a polyhydroxypolyamino compound. It is preferred that 50 mol % or more of the whole functional groups of such a polyhydroxy compound or polyamino compound have been substituted with quinone diazide. It is preferred that two or more kinds of photo acid generators (d) be contained and a highly photosensitive resin composition can be obtained.
- In the present invention, a quinone diazide compound that has any of a 5-naphthoquinone diazide sulfonyl group and a 4-naphthoquinone diazide sulfonyl group is preferably used. A 4-naphthoquinonediazide sulfonyl ester compound is suitable for i-line exposure because it has an absorption in the i-line region of a mercury lamp. A 5-naphthoquinonediazide sulfonyl ester compound is suitable for g-line exposure because it has an absorption extending to the g-line region of a mercury lamp. In the present invention, it is preferred to choose a 4-naphthoquinonediazide sulfonyl ester compound and a 5-naphthoquinonediazide sulfonyl ester compound depending upon the wavelength of light to be applied. A naphthoquinonediazide sulfonyl ester compound that has a 4-naphthoquinone diazide sulfonyl group and a 5-naphthoquinone diazide sulfonyl group in the same molecule may be contained, and both a 4-naphthoquinonediazide sulfonyl ester compound and a 5-naphthoquinonediazide sulfonyl ester compound may be contained.
- Among photo acid generators (d), sulfonium salt, phosphonium salts, diazonium salts are preferred because they moderately stabilize the acid component generated by exposure to light. Particularly, sulfonium salts are preferred.
- In the present invention, from the viewpoint of enhancement in sensitivity, the content of the photo acid generator (d) is preferably 0.01 to 50 parts by weight relative to 100 parts by weight of the resin of component (a). Among these, the range of 3 to 40 parts by weight is preferred for a quinone diazide compound. The total amount of the sulfonium salt, the phosphonium salt, and the diazonium salt is preferably within the range of 0.5 to 20 parts by weight. Furthermore, a sensitizing agent or the like can also be contained according to need. When containing two or more kinds of component (d), their total amount is preferably within the above-mentioned range.
- The photosensitive resin composition of the present invention may further comprise (e) a photopolymerization initiator and (f) a compound having two or more ethylenically unsaturated bonds. It is possible to obtain a negative type relief pattern in which active radicals generated in the part exposed to light advance the radical polymerization of ethylenically unsaturated bonds, so that the part exposed to light becomes insoluble.
- Examples of (e) the photopolymerization initiator include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexyl-phenyl ketone, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, 2-methyl-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4,4-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4′-methyl-diphenyl sulfide, alkylated benzophenone, 3,3′,4,4′-tetra(tert-butylperoxycarbonyl)benzophenone, 4-benzoyl-N,N-dimethyl-N-[2-(1-oxo-2-propenyloxy)ethyl]benz ene methanaminium bromide, (4-benzoylbenzyl)trimethylammonium chloride, 2-hydroxy-3-(4-benzoylphenoxy)-N,N,N-trimethyl-1-propene aminium chloride monohydrate, 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthen-2-yloxy)-N,N,N-trimethyl-1-propanaminium chloride, 2,4,6-trimethylbenzoylphenylphosphine oxide, 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyloxime)], ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime), 2,2′-bis (o-chlorophenyl)-4,5,4′,5′-tetraphenyl-1,2-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzil, 9,10-phenanthrenequinone, camphorquinone, methylphenylglyoxy ester, η5-cyclopentadienyl-eta6-cumenyl-iron(1+)-hexafluorophosphate(1−), diphenylsulfide derivatives, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, 4-benzoyl-4-methylphenyl ketone, dibenzyl ketone, fluorenone, 2,3-diethoxyacetophenone, 2,2-dimethoxy-2-phenyl-2-phenylacetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyldichloroacetophenone, benzilmethoxyethyl acetal, anthraquinone, 2-tert-butyl anthraquinone, 2-aminoanthraquinone, β-chloroanthraquinone, anthrone, benzanthrone, dibenzsuberone, methyleneanthrone, 4-azidobenzalacetophenone, 2,6-bis(p-azidobenzyliene)cyclohexane, 2,6-bis(p-azidobenzyliene)-4-methylcyclohexanone, 2-phenyl-1,2-butadione-2-(o-methoxycarbonyl)oxime, 1,3-diphenylpropanetrione-2-(o-ethoxycarbonyl)oxime, naphthalenesulfonyl chloride, quinolinesulfonyl chloride, N-phenylthioacridone, 4,4-azobisisobutyronitrile, benzthiazole disulfide, triphenylphosphine, tetrabromocarbon, tribromophenylsulfone, benzoyl peroxide, and combinations of photoreductive dyes, such as eosin and methylene blue, and reducing agent, such as ascorbic acid and triethanolamine. Two or more of these may be contained.
- In the present invention, the content of the photopolymerization initiator (e) is preferably 0.1 to 20 parts by weight relative to 100 parts by weight of the resin of component (a). If it is 0.1 parts by weight or more, a sufficient amount of radical is generated by irradiation with light and photosensitivity increases. If it is 20 parts by weight or less, curing of a part unexposed to light caused by the generation of excessive radicals does not occur, resulting in increase in alkali developability. When containing two or more kinds of component (e), their total amount is preferably within the above-mentioned range.
- Examples of the compound having two or more ethylenically unsaturated bonds (f) include acrylic monomers such as ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate, trimethylolpropane triacrylate, ethoxylated bisphenol A dimethacrylate, glycerin dimethacrylate, tripropylene glycol dimethacrylate, butanediol dimethacrylate, glycerin triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ethoxylated pentaerythritol tetraacrylate, and ethoxylated isocyanuric acid triacrylate. Two or more of these may be contained.
- In the present invention, the content of the compound having two or more ethylenically unsaturated bonds (f) is preferably 1 part by weight or more, and more preferably 5 parts by weight of more relative to 100 parts by weight of the resin of component (a). It is preferably 100 parts by weight or less, and more preferably 50 parts by weight or less. When containing two or more kinds of component (f), their total amount is preferably within the above-mentioned range.
- For the purpose of adjustment of solubility or the like, a compound having only one ethylenically unsaturated bond may be contained in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the resin of component (a). Examples of such a compound include acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, dimethylacrylamide, dimethylaminoethyl methacrylate, acryloylmorpholin, 1-hydroxyethyl alpha-chloroacrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl α-chloroacrylate, 1-hydroxypropyl methacrylate, 1-hydroxypropyl acrylate, 1-hydroxypropyl α-chloroacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl α-chloroacrylate, 3-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl α-chloroacrylate, 1-hydroxy-1-methylethyl methacrylate, 1-hydroxy-1-methylethyl acrylate, 1-hydroxy-1-methylethyl α-chloroacrylate, 2-hydroxy-1-methylethyl methacrylate, 2-hydroxy-1-methylethyl acrylate, 2-hydroxy-1-methylethyl α-chloroacrylate, 1-hydroxybutyl methacrylate, 11-hydroxybutyl acrylate, 1-hydroxybutyl α-chloroacrylate, 2-hydroxybutyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl α-chloroacrylate, 3-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl α-chloroacrylate, 4-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl α-chloroacrylate, 1-hydroxy-1-methylpropyl methacrylate, 1-hydroxy-1-methylpropyl acrylate, 1-hydroxy-1-methylpropyl α-chloroacrylate, 2-hydroxy-1-methylpropyl methacrylate, 2-hydroxy-1-methylpropyl acrylate, 2-hydroxy-1-methylpropyl α-chloroacrylate, 1-hydroxy-2-methylpropyl methacrylate, 1-hydroxy-2-methylpropyl acrylate, 1-hydroxy-2-methylpropyl α-chloroacrylate, 2-hydroxy-2-methylpropyl methacrylate, 2-hydroxy-2-methylpropyl acrylate, 2-hydroxy-2-methylpropyl α-chloroacrylate, 2-hydroxy-1,1-dimethylethyl methacrylate, 2-hydroxy-1,1-dimethylethyl acrylate, 2-hydroxy-1,1-dimethylethyl α-chloroacrylate, 1,2-dihydroxypropyl methacrylate, 1,2-dihydroxypropyl acrylate, 1,2-dihydroxypropyl α-chloroacrylate, 2,3-dihydroxypropyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl α-chloroacrylate, 2,3-dihydroxybutyl methacrylate, 2,3-dihydroxybutyl acrylate, 2,3-dihydroxybutyl α-chloro acrylate, p-hydroxystyrene, p-isopropenylphenol, phenethyl methacrylate, phenethyl acrylate, phenethyl α-chloroacrylate, N-methylolacrylamide, N-methylolmethacrylamide, α-chloroacrylic acid, crotonic acid, 4-pentenoic acid, 5-hexenoic acid, 6-heptenoic acid, 7-octenoic acid, 8-nonanoic acid, 9-decanoic acid, 10-undecylenic acid, brassidic acid, ricinoleic acid, 2-(methacryloxy)ethyl isocyanate, 2-(acryloyloxy)ethyl isocyanate, and 2-(c-chloroacryloyloxy)ethyl isocyanate. Two or more of these may be contained.
- The resin composition of the present invention may further contain (g) a thermal acid generator. The thermal acid generator (g) generates an acid on heating after development described later, so that it promotes a cross-linking reaction of the resin of component (a) with the thermal cross-linking agent of component (c) and also promotes the cyclization of the imide ring or the oxazole ring of the resin of component (a). This offers the improvement in chemical resistance of a cured film and successfully reduces film loss. The acid to be generated from the thermal acid generator (g) is preferably a strong acid and, for example, aryl sulfone acids, such as p-toluenesulfonic acid and benzenesulfonic acid, and alkyl sulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, and butanesulfonic acid, are preferred. In the present invention, the thermal acid generator preferably is an aliphatic sulfonic acid compound represented by formula (4) or (5) and it may contain two or more kinds of such compounds.
- [kagaku 11]
- In the above formulae (4) and (5), R30 to R32 each represent an alkyl group having 1 to 10 carbon atoms or a monovalent aromatic group having 7 to 12 carbon atoms. The alkyl group and the aromatic group may be substituted and examples of a substituent include an alkyl group and a carbonyl group.
- Specific examples of the compound represented by formula (4) include the following compounds.
- [kagaku 12]
- Specific examples of the compound represented by formula (5) include the following compounds.
- [kagaku 13]
- From the viewpoint of promoting a cross-linking reaction, the content of the thermal acid generator (g) is preferably 0.1 parts by weight or more, more preferably 0.3 parts by weight or more, and even more preferably 0.5 parts by weight or more relative to 100 parts by weight of the resin of component (a). On the other hand, from the viewpoint of the electrically insulating property of a cured film, it is preferably 20 parts by weight or less, more preferably 15 parts by weight or less, and even more preferably 10 parts by weight or less. When containing two or more kinds of component (g), their total amount is preferably within the above-mentioned range.
- The resin composition of the present invention can contain (h) a filler. In the case of using the resin composition of the present invention as a solder resist for circuit boards, the inclusion of the filler (h) has an effect of exhibiting thixotropy to maintain a pattern at a prescribed size in the course of coating the composition by screen printing and drying it. Moreover, an effect to control shrinkage caused by heat curing is also expectable.
- Among fillers (h), examples of insulative fillers include calcium carbonate, silica, alumina, aluminum nitride, titanium oxide, andsilica-titaniumoxide composite particles, and silica, titanium oxide, and silica-titanium oxide composite particles are preferred. Examples of the electrically conductive filler include gold, silver, copper, nickel, aluminum, and carbon, and silver is preferred. Two or more of these may be contained depending upon the intended application. The content of the filler (h) is preferably within the range of 5 to 500 parts by weight relative to 100 parts by weight of component (a). The number average particle diameter of the filler (h) is preferably 10 μm or less and more preferably 2 μm or less. The use of two or more fillers differing in number average particle diameter in combination is also preferred from the viewpoint of imparting thixotropy and stress relaxation.
- The use of particles having a number average particle diameter of 100 nm or less, which are so-called nanoparticles, as the filler (h) makes it possible to adjust physical properties such as index of refraction while maintaining light transmittance. Particularly, the use of nanoparticles with a high index of refraction makes it possible to develop a high transmittance and a high index of refraction simultaneously. The mixing of such nanoparticle makes it possible to be used suitably as a low-temperature-curable optical thin film, such as an on-chip microlens of a solid imaging element and a planarization film for displays and solid imaging elements. Examples of particles suitable for the above-mentioned purpose include tin oxide-aluminum oxide mixed particles, zirconium oxide-aluminum oxide mixed particles, zirconium oxide-silicon oxide mixed particles, tin oxide particles, zirconium oxide-tin oxide mixed particles, titanium oxide particles, tin oxide-titanium oxide mixed particles, silicon oxide-titanium oxide mixed particles, zirconium oxide-titanium oxide mixed particles, and zirconium oxide particles. The surface of particles may be coated with another substance. Although the above-mentioned particles may be either in the form of a powder or in the form of sol, they are preferably in the form of sol from the viewpoint of easiness with which they are dispersed. In view of transmittance, the number average particle diameter of the nanoparticles is preferably 50 nm or less and more preferably 30 nm or less.
- The number average particle diameter of a filler can be measured by using various particle counters. The average particle diameter of nanoparticles can be measured by, for example, a gas adsorption method, a dynamic light scattering method, an X-ray small angle scattering method, or a method of measuring particle diameters directly with a transmission electron microscope. Although the particle diameter obtained by these measuring methods may be in volume average or in mass average, it can be converted into a number average molecular weight with the assumption that the shape of a particle is spherical.
- The resin composition of the present invention can contain a thermally coloring compound that colors on heating to exhibit an absorbance maximum at 350 nm or longer and 700 nm or shorter or an organic pigment or dyestuff that has no absorbance maximum at 350 nm or longer and shorter than 500 nm and has an absorbance maximum at 500 nm or longer and 750 nm or shorter. The coloring temperature of the thermally coloring compound is preferably 120° C. or higher and more preferably is 150° C. or higher. The heat resistance under high temperature conditions becomes better and the light resistance becomes better without the occurrence of fading due to prolonged ultraviolet-visible light irradiation as the coloring temperature of the thermally coloring compound becomes higher.
- Examples of the thermally coloring compound include heat-sensitive dyes, pressure-sensitive dyes, and hydroxyl group-containing compounds having a triarylmethane skeleton.
- The resin composition of the present invention may contain an adhesion promoter. Examples of the adhesion promoter include silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimetoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryl trimethoxysilane, 3-aminopropyl trimethoxysilane, 3-aminopropyltriethoxysilane, and N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, compounds to be obtained by reacting an aromatic amine compound with an alkoxy group-containing silicon compound. Two or more of these may be contained. Inclusion of such adhesive promoters can enhance the adhesion property with a base substrate, such as a silicon wafer, ITO, SiO2, and silicon nitride, when, for example, developing a photosensitive resin film. Moreover, it is possible to enhance resistance to oxygen plasma and UV ozone treatment to be used for washing or the like. The content of the adhesion promoter is preferably 0.1 to 10 parts by weight per 100 parts by weight of the resin of component (a).
- The resin composition of the present invention may contain an adhesion promoter. Examples of the adhesion promoter include alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, and non-aromatic silane compounds. Two or more of these may be contained. Inclusion of such compounds can improve the adhesive property with a substrate after curing. Specific examples of the alkoxysilane-containing aromatic amine compounds and aromatic amide compounds are provided below. In addition, compounds obtainable by reacting an aromatic amine compound with an alkoxy group-containing silicon compound can also be used and examples thereof include compounds obtainable by reacting an aromatic amine compound with an alkoxysilane compound has a group that reacts with an amino group, such as an epoxy group and a chloromethyl group.
- [kagaku 14]
- Examples of the non-aromatic silane compounds include vinyl silane compounds, such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyl trichlorosilan, and vinyltris(β-methoxyethoxy)silane, and carbon-carbon unsaturated bond-containing silane compounds, such as 3-methacryloxypropyltrimethoxysilane, 3-acryloxyprophyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane. Among these, vinyltrimethoxysilane and vinyltriethoxysilane are preferred.
- The total content of the alkoxysilane-containing aromatic amine compound, the aromatic amide compound, or the non-aromatic silane compound is preferably 0.01 to 15 parts by weight relative to 100 parts by weight of the resin of component (a).
- The resin composition of the present invention may contain a surfactant, by which the wettability with a substrate can be improved.
- Examples of the surfactant include fluorine-based surfactants, such as Fluorad (commercial name, available from Sumitomo 3M Ltd.), MEGAFAC (commercial name, available from DIC Corporation), and Sulfron (commercial name, available from Asahi Glass Co., Ltd.), organic siloxane surfactants, such as KP341 (commercial name, available from Shin-Etsu Chemical Co., Ltd.), DBE (commercial name, Chisso Corporation), POLYFLOW, GLANOL (commercial names, available from Kyoeisha Chemical Co., Ltd.), and BYK (available from BYK-Chemie), and acrylic polymer surfactants, such as POLYFLOW (commercial name, available from Kyoeisha Chemical Co., Ltd.).
- The resin composition of the present invention preferably contains a solvent. Examples of the solvent include polar aprotic solvents, such as N-methyl-2-pyrrolidone, γ-butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide, ethers, such as tetrahydrofuran, dioxane, propylene glycol monomethyl ether, and propylene glycol monoethyl ether, ketones, such as acetone, methyl ethyl ketone, diisobutyl ketone, and diacetone alcohol, esters, such as ethyl acetate, butyl acetate, isobutyl acetate, propyl acetate, propylene glycol monomethyl ether acetate, and 3-methyl-3-methoxy butyl acetate, alcohols, such as ethyl lactate, methyl lactate, diacetone alcohol, and 3-methyl-3-methoxybutanol, aromatic hydrocarbons, such as toluene and xylene. Two or more of these may be contained. The content of the solvent is preferably 100 to 2000 parts by weight relative to 100 parts by weight of the resin of component (a).
- It is preferred for the resin composition of the present invention that the transmittance of a resin film before curing be high and the transmittance in the visible region of a cured film be low. Specifically, it is preferred that the change in transmittance at a wavelength of 450 nm before and after curing in a 3.0 μm thick film be 20% or more. Here, the transmittance at a wavelength of 450 nm is an index of the transmittance in the visible region. More specifically, it is preferred that the transmittance change be 20% or more, which is calculated by the following formula from the transmittance at a wavelength of 450 nm of a 3.0 μm thick film (before curing) to be obtained by coating a resin composition to a substrate and then heat-treating it at 120° C. for 2 minutes and the transmittance at a wavelength of 450 nm of a 3.0 μm thick film (after curing) to be obtained by further heat-treating the film before curing, at 230° C. for 30 minutes under nitrogen flow. The present invention makes it possible to realize such a change in transmittance easily.
-
Change in transmittance (%)=transmittance before curing (%)−transmittance after curing (%) - In the case of using the resin composition of the present invention as a photosensitive resin, it is preferred that the transmittance of a resin film before curing be high. Specifically, the transmittance at a wavelength of 450 nm of a resin film before curing is preferable 70% or more and more preferably 90% or more. It is preferred that the transmittance in the visible region of a cured film be low. Specifically, the transmittance at a wavelength of 450 nm of a cured film is preferable 70% or less and more preferably 60% or less. In the case of using the resin composition of the present invention for a planarization film or a dielectric film of a display device, it is possible to prevent malfunction caused by penetration of light to a TFT for driving, a leak electric current, or the like by adjusting the transmittance of a cured film to be low. For this reason, the change in transmittance at a wavelength of 450 nm before and after curing is preferably 20% to 100% and more preferably 30% to 100%.
- Next, the method for producing the resin composition of the present invention is described. For example, a resin composition can be obtained by dissolving the aforementioned components (a) to (c) and, if necessary, components (d) to (h), a thermally coloring component, an adhesion promoter, an adhesion promoter, a surfactant, or the like in a solvent. Examples of the dissolving method include agitation and heating. In the case of heating, it is preferred to adjust the heating temperature as far as the performance of a resin composition is not impaired and it is usually from room temperature to 80° C. The order of dissolving components is not particularly limited and, for example, there is method of dissolving them one after another from a compound lower in solubility. As for a component that is prone to generate bubbles during dissolution by agitation, such as surfactants and some adhesion promoters, imperfect dissolution of other components due to the generation of bubbles can be prevented by dissolving the other components and lastly adding that component.
- It is preferred to filter the resulting resin composition with a filter to remove dusts or particles. The hole diameter of the filter is, for example, but is not limited to, 0.5 μm, 0.2 μm, 0.1 μm, and 0.05 μm. Examples of the material of the filter includepolypropylene (PP), polyethylene (PE), nylon (NY), and polytetrafluoroethylene (PTFE), and polyethylene and nylon are preferred. When the resin composition contains (h) a filler or an organic pigment, it is preferred to use a filter having a pore diameter larger than the particle diameter of them.
- Next, the method for producing a cured film using the resin composition of the present invention is described. A resin composition film is obtained by coating the resin composition of the present invention by a spin coating method, a slit coating method, a dip coating method, a spray coating method, a printing method, or the like. In advance of coating, the substrate to which the resin composition is to be coated may be pretreated with the adhesion promoter mentioned above. For example, there is a method of treating a substrate surface by using a solution in which 0.5 to 20% by weight of an adhesion promoter has been dissolved in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and diethyl adipate. Examples of the method of treating the substrate surface include spin coating, slit die coating, bar coating, dip coating, spray coating, and vapor treatment. According to need, it is permitted to advance a reaction between the substrate and the adhesion promoter by conducting drying treatment under reduced pressure and then conducting heat treatment of 50° C. to 300° C.
- A cured film can be obtained by thermally treating a resulting resin composition film. For example, a method of performing heat treatment at 230° C. for 60 minutes, a method of performing heat treatment at 120 to 400° C. for 1 minute to 10 hours, a method of performing heat treatment at a low temperature of from room temperature to about 100° C. with addition of a curing catalyst or the like, and a method of performing curing at a low temperature of from room temperature to about 100° C. by a supersonic wave or electromagnetic wave treatment are mentioned.
- When the resin composition of the present invention has photosensitivity, a negative type or positive type relief pattern can be obtained by irradiating the above-mentioned resin composition film partially with active light, such as an ultraviolet ray, and performing developing treatment with a developing solution.
- A cured film obtained by curing the resin composition of the present invention is suitably used as a dielectric film or a protective film of wires. For example, there are an application for a dielectric film or a protective film of wires in a printed board in which wires are formed from copper, aluminum, or the like on a film or a substrate of a polyimide and ceramics, and an application for a protective film for partly soldering wires. When the resin composition contains an electrically conductive filler, it can also be used as a wire material.
- Moreover, a cured film obtained by curing the resin composition of the present invention is suitably used as a planarization film or a dielectric layer of a display device having a substrate with a TFT formed thereon, a planarization film, a dielectric layer, and a display element in this order. Examples of a display device of this constitution include a liquid crystal display device and an organic EL display device. An active matrix type display device has a TFT on a substrate of glass or the like and wires located in a side portion of the TFT and connected to the TFT and has a planarization film thereon so that it may cover the irregularities of the wires, and it is further provided with a display element on the planarization film. The display element and the wires are connected via a contact hole formed in the planarization film.
FIG. 1 shows a sectional view of a TFT substrate in which a planarization film and a dielectric layer have been formed. A bottom gate type or topgate type TFT 1 in matrix form has been provided on asubstrate 6 and adielectric film 3 has been formed with theTFT 1 covered therewith. Awire 2 connected to theTFT 1 has been provided under thedielectric film 3. Furthermore, on thedielectric film 3 have been provided a contact hole that opens thewire 2 and aplanarization film 4 with the wire and the contact hole embedded. Theplanarization film 4 has been provided with an opening so as to reach thecontact hole 7 of thewire 2. Moreover, an ITO (transparent electrode) 5 has been formed on theplanarization film 4 in connection with thewire 2 via thecontact hole 7. Here, theITO 5 serves as an electrode of a display element (for example, organic EL element). In addition, adielectric layer 8 is formed so that the periphery of theITO 5 may be covered. This organic EL element may be either a top emission type which emits light from the side opposite to thesubstrate 6 or a bottom emission type which extracts light from the side of thesubstrate 6. In the above-described manner, an active matrix type organic EL display device in which the organic EL elements each have been connected to aTFT 1 for driving them. - Moreover, a cured film obtained by curing the resin composition of the present invention is suitably used as a dielectric layer of a display device having a substrate with a TFT formed thereon, a dielectric layer, and a display element in this order. Examples of a display device having such a constitution include organic EL display devices. An active matrix type display device has a TFT on a substrate of glass or the like, and wires located in a side part of the TFT and connected to the TFT. The display element and the wires are connected via a contact hole formed in the dielectric film.
FIG. 2 shows a sectional view of a TFT substrate in which a dielectric layer has been formed. A bottom gate type or topgate type TFT 1 in matrix form has been provided on asubstrate 6 and adielectric film 3 has been formed with theTFT 1 covered therewith. Awire 2 connected to theTFT 1 has been provided under thedielectric film 3. Moreover, acontact hole 7 has been formed on thedielectric film 3 so that it may open thewire 2. An ITO (transparent electrode) 5 has been formed in connection with thewire 2 via thecontact hole 7. Here, theITO 5 serves as an electrode of a display element (for example, organic EL element). Adielectric layer 8 is formed so that the periphery of theITO 5, the TFT, and the steps of the wires may be covered. This organic EL element may be either a top emission type which emits light from the side opposite to thesubstrate 6 or a bottom emission type which extracts light from the side of thesubstrate 6. In the above-described manner, an active matrix type organic EL display device in which the organic EL elements each have been connected to aTFT 1 for driving them. - For example, in the case of an organic EL display device using a TFT comprising, for example, amorphous silicone, micro crystal silicon, or an oxide semiconductor typified by In—Ga—Zn—O, unfavorable phenomena, such as a leak electric current or a photoinduced electric current, may be caused due to penetration of blue light with a relatively high energy. Since a cured film obtainable from the resin composition of the present invention has a moderate absorption near 450 nm, the occurrence of a leak electric current, a photoinduced electric current, or the like is prevented and a stable driving/light emission characteristic is obtained by using for a dielectric layer, a planarization film, etc. in such an organic electroluminescence display device.
- Moreover, a cured film to be obtained by curing the resin composition of the present invention can be used suitably for such applications as a surf ace protective film of a semiconductor element, such as LSI, an interlayer dielectric film, and an adhesive and an under fill agent for packing a device into a package, a capping agent that prevents copper migration, an on-chip microlens of a solid imaging element, and a planarization film for displays and solid imaging elements.
- The present invention will be described below with reference to examples, but the invention is not limited by these examples.
- The evaluations of the resin compositions in examples were carried out by the following methods.
- (1) Evaluation of Transmittance
- A resin composition (hereinafter referred to as a varnish) was spin coated onto a 5 cm square glass substrate and was subjected to heat treatment (prebaking) at 120° C. for 2 minutes, so that a prebaked film having a thickness of 3.0 μm was produced. A varnish was spin coated so that its film thickness after curing might become 3.0 μm, and then heat treatment was carried out for 30 minutes at 230° C. under nitrogen flow (
oxygen concentration 20 ppm or less) using an Inert Gas Oven INH-21CD available from Koyo Thermo Systems Co., Ltd., so that a cured film was produced. The thicknesses of the prebaked film and the cured film were measured using a SURFCOM 1400D (available from Tokyo Seimitsu Co., Ltd.). For each of the thus obtained prebaked film and cured film, a transmission spectrum at wavelengths of 300 nm to 700 nm was measured using a UV-VIS spectrophotometer Multi-Spec-1500 (available from Shimadzu Corporation) and a transmittance at a wavelength of 450 nm was measured. From a transmittance before curing (=prebaked film) and that after curing (=cured film), a change in transmittance was calculated using the following formula. -
Change in transmittance (%)=transmittance before curing (%)−transmittance after curing (%) - When the change in transmittance is equal to or more than 20%, a judgment as being good can be provided and when it is equal to or more than 30%, a judgment as being very good can be provided.
- (2) Evaluation of Sensitivity
- The varnishes prepared in Examples 4 to 11 and Comparative Examples 5 to 6 were each rotation coated onto a 6-inch silicon wafer and then heat-treated for 3 minutes on a hot plate (Mark-7), so that 4.0 μm thick prebaked films were produced. The prebaking temperature was adjusted to 120° C. for Examples 4 to 9 and Comparative Examples 5 to 6 and 100° C. for Examples 10 to 11. The resulting prebaked films were exposed with an exposure of 0 to 500 mJ/cm2 at a 25 mJ/cm2 step using an i-line stepper (DSW-8000, available from GCA). The line & space patterns used for the exposure are 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 50 and 100 μm. In Examples 10 to 11, heating was carried out at 100° C. for 1 minute after the exposure. After the exposure for Examples 4-9 or after the exposure and the following heating for Examples 10 to 11, development was performed in a 2.38 wt % aqueous solution of tetramethylammonium (TMAH) (ELM-D, available from Mitsubishi Gas Chemical Co., Inc.) for 60 seconds, followed by rinsing with pure water, so that developed films were obtained. In the case of a positive type varnish, an exposure at which the exposed part was dissolved and disappeared through the development was defined as a photosensitivity. In the case of a negative type varnish, the thickness of a film after development was measured and an exposure at which 90% of the thickness of a prebaked film remained was defined as a photosensitivity. The thickness after prebaking and that after development were measured using a Lambda Ace STM-602 available from Dainippon Screen Mfg. Co., Ltd. at an index of refraction of 1.63.
- (3) Evaluation of Chemical Resistance
- (i) The varnishes prepared in Examples 1 to 3 and Comparative Examples 1 to 4 were each spin coated out onto a 6 inch silicon wafer and then heat-treated for 3 minutes on a hot plate, so that 4.0 μm thick prebaked films were produced. On the other hand, films after development were produced from the varnishes prepared in Examples 4 to 11 and Comparative Examples 5 to 6 by the method described in the foregoing (2). The resulting prebaked films and film after development were heat-treated at 230° C. for 30 minutes under nitrogen flow (
oxygen concentration 20 ppm or less) using an Inert Oven INH-21CD available Koyo Thermo Systems Co., Ltd., so that cured films were produced. - The resulting cured films were immersed in a stripping liquid 106 available from Tokyo Ohka Kogyo Co., Ltd. at 70° C. for 10 minutes. The thickness of a cured films before the stripping liquid treatment and the thickness of a cured film after that treatment were measured using a Lambda Ace STM-602 available from Dainippon Screen Mfg. Co., Ltd. at an index of refraction of 1.64, and then the reduction in film thickness was calculated. The reduction in film thickness is preferably 0.25 μm or less, more preferably 0.15 μm or less, and even more preferably 0.10 μm or less.
- (ii) Cured films were produced by the method described in the foregoing (i) using the varnishes prepared in Examples 4 to 11 and Comparative Examples 5 to 6. The resulting cured films were immersed in a stripping liquid 106 available from Tokyo Ohka Kogyo Co., Ltd. at 70° C. for 10 minutes. A cured film after the stripping liquid treatment was observed with an optical microscope of 20 magnifications, so that the presence of coming off of a pattern was evaluated. The smallest pattern having no coming off of a pattern was defined as being a remaining pattern. Since the finer a pattern becomes, the more likely it comes off, when a remaining pattern is equal to or less than 20 μm, a judgment as being good can be provided and when it is equal to or less than 5 μm, a judgment as being very good can be provided.
- 18.3 g (0.05 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (BAHF, available from Central Glass Co., Ltd.) was dissolved in 100 mL of acetone and 17.4 g (0.3 mol) of propylene oxide (available from Tokyo Chemical Industry Co., Ltd.), followed by cooling to −15° C. A solution in which 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride (available from Tokyo Chemical Industry Co. Ltd.) had been dissolved in 100 mL of acetone was dropped here. After the completion of the dropping, agitation was done at −15° C. for 4 hours and then the temperature was returned to room temperature. The precipitated white solid was collected by filtration and then was vacuum dried at 50° C.
- 30 g of the resulting white solid was placed in a 300 mL stainless steel autoclave and was dispersed in 250 mL of methyl cellosolve, followed by the addition of 2 g of 5% palladium-carbon (available from Wako Pure Chemical Industries, Ltd.). Hydrogen was introduced here with a balloon and a reduction reaction was performed at room temperature. About 2 hours later, the reaction was terminated on confirmation of the fact that the balloon no longer shrank. After the termination of the reaction, the palladium compound, the catalyst, was removed by filtration, followed by concentration with a rotary evaporator, affording a hydroxyl group-containing diamine compound represented by the following formula.
- [kagaku 15]
- Under dry nitrogen flow, 21.22 g (0.05 mol) of TrisP-PA (commercial name, available from Honshu Chemical Industry Co., Ltd.) and 26.8 g (0.1 mol) of 5-naphthoquinonediazidosulfonyl chloride (NAC-5, available from Toyo Gosei Co., Ltd.) were dissolved in 450 g of 1,4-dioxane and the temperature was adjusted to room temperature. 12.65 g of triethylamine, which had been mixed with 50 g of 1,4-dioxane, was dropped here so that the temperature of the system might not become equal to or higher than 35° C. After the dropping, agitation was done at 40° C. for 2 hours. A triethylamine salt was filtered and the filtrate was poured into water. Then a precipitate formed was collected by filtration and washed with 1 L of 1% aqueous hydrochloric acid. Then it was further washed with 2 L of water twice. The precipitation was dried in a vacuum dryer, so that a quinone diazide compound represented by the following formula was obtained.
- [kagaku 16]
- (1) 103.2 g (0.4 mol) of 1,1,1-tris (4-hydroxyphenyl)ethane (TrisP-HAP, available from Honshu Chemical Industry Co., Ltd.) was dissolved in a solution in which 80 g (2.0 mol) of sodium hydroxide had been dissolved in 800 g of pure water. After the complete dissolution, 686 g of 36-38 wt % formalin was dropped at 20 to 25° C. over 2 hours. Then agitation was done at 20 to 25° C. for 17 hours. This was neutralized by adding 98 g of sulfuric acid and 552 g of water and then was left at rest for 2 days. A needlelike white crystal formed after being left at rest was collected by filtration and then was washed with 100 mL of water. The white crystal was vacuum dried at 50° C. for 48 hours. When the dried white crystal was analyzed by a high-performance liquid chromatograph available from Shimadzu Corporation at 254 nm using ODS as a column, acetonitrile/water=70/30 as a developing solvent, it was found that the starting material had disappeared completely and the purity was 92%. Moreover, when analysis was done by NMR (GX-270, available from JEOL Ltd.) using DMSO-d6 as a deuterated solvent, it was found to be hexamethyloled TrisP-HAP.
- (2) Next, the compound thus obtained was dissolved in 300 mL of methanol and was agitated at room temperature for 24 hours after the addition of 2 g of sulfuric acid. To this solution was added 15 g of an anionic ion exchange resin (Amberlyst IRA96SB, available from Rohm and Haas), followed by agitation for 1 hour. Then the ion exchange resin was removed by filtration. After that, 500 mL of ethyl lactate was added and methanol was removed by a rotary evaporator, so that an ethyl lactate solution was formed. This solution was left at rest at room temperature for 2 days, so that a white crystal generated. When the obtained white crystal was analyzed by high-performance liquid chromatography, it was found to be a hexamethoxymethyl compound of TrisP-HAP (alkoxymethyl group-containing compound (A-1)) represented by the following formula having a purity of 99%.
- [kagaku 17]
- (1) A dry white crystal was obtained in the same manner as in Synthesis Example 3(1) except for using 169.6 g (0.4 mol) of 4,4′-[1-[4-[1-(4-hydroxyphenyl-1)-1-methylethyl]phenyl]ethylidene]bisphenol (TrisP-PA, available from Honshu Chemical Industry Co., Ltd.) instead of 103.2 g (0.4 mol) of 1,1,1-tris (4-hydroxyphenyl)ethane (TrisP-HAP, available from Honshu Chemical Industry Co., Ltd.). This was analyzed by high-performance liquid chromatography in the same manner as in Synthesis Example 3 (1) to be found that the starting materials had disappeared completely and the purity was 88%. Moreover, it was subjected to NMR analysis in the same manner as in Synthesis Example 3 (1), thereby being found to be hexamethyloled TrisP-PA.
- (2) Next, a white crystal was obtained in the same manner as in Synthesis Example 3(2) except for using hexamethyloled TrisP-PA obtained by the described method instead of the hexamethyloled TrisP-HAP. The obtained white crystal was analyzed by high-performance liquid chromatography to be a hexamethoxymethyl compound of TrisP-PA (alkoxymethyl group-containing compound (A-2)) represented by a following formula having a purity of 99%.
- [kagaku 18]
- (1) Hexamethyloled TrisP-HAP having a purity of 92% was obtained in the same manner as in Synthesis Example 3(1).
- (2) Next, a white crystal was obtained in the same manner as in Synthesis Example 3 (2) except for using 300 mL of ethanol instead of 300 mL of methanol. The obtained white crystal was analyzed by high-performance liquid chromatography to be a ethoxymethyl compound of TrisP-HAP (alkoxymethyl group-containing compound (A-3)) represented by a following formula having a purity of 98%.
- [kagaku 19]
- 36.6 g (0.1 mol) of BAHF (available from Central Glass Co., Ltd.) was dissolved in 100 g of ethyl lactate (EL, available from Musashino Chemical Laboratory, Ltd.). Subsequently, 55.6 g (0.2 mol) of 3-glycidoxypropyltriethoxysilane (KBE-403, available from Shin-Etsu Chemical Co., Ltd.) was added to this solution and agitated at 50° C. for 6 hours, so that adhesion promoter (B-1) was obtained.
- Other thermal cross-linking agents and acid generators used in the Examples and the Comparative Examples are as follows.
- [kagaku 20]
- 32.9 g (0.09 mol) of BAHF was dissolved in 500 g of N-methyl pyrrolidone (NMP) under dry nitrogen flow. Here was added 31.0 g (0.1 mol) of 3,3′,4,4′-diphenyl ether tetracarboxylic dianhydride (ODPA, available from Manac Incorporated) together with 50 g of NMP, followed by agitation at 30° C. for 2 hours. Then 2.18 g (0.02 mol) of 3-aminophenol (available from Tokyo Chemical Industry Co. Ltd.) was added and agitation was continued at 40° C. for 2 hours. In addition, 5 g of pyridine (available from Tokyo Chemical Industry Co. Ltd.) was diluted in toluene (30 g, available from Tokyo Chemical Industry Co. Ltd.) and was added to the solution, and then a cooling tube was attached and a reaction was carried out for 2 hours with the temperature of the solution kept at 120° C. and further for 2 hours at 180° C. while azeotropically removing water together with toluene out of the system. The temperature of this solution was dropped to room temperature and the solution was poured into 3 L of water, so that a white powder was obtained. This powder was collected by filtration and further was washed with water three times. After the washing, the white powder was dried in a vacuum dryer of 50° C. for 72 hours, so that a polyimide was obtained.
- To 10 g of the polyimide were added 4 g of 1,5-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compounds (A-1) obtained in Synthesis Example 3, and 40 g of gamma-butyrolactone (GBL, available from Mitsubishi Chemical Corporation), so that a varnish of a polyimide resin composition was obtained. As to the transmittance at 450 nm of a film obtained using this varnish measured before or after curing, the transmittance before curing was 95% and that after curing was 61%. This means that the change in transmittance was 34%. When the chemical resistance of the cured film was evaluated, the reduction in film thickness was 0.10 μm or less and therefore the chemical resistance was very good.
- A varnish of a polyimide resin composition was obtained in the same manner as in Example 1 except for adding 5 g of 2,6-dimethoxymethyl-t-butylphenol (available from Honshu Chemical Industry Co., Ltd.) instead of the alkoxymethyl group-containing compound (A-1) obtained in Synthesis Example 3. As to the transmittance at 450 nm of a film obtained using this varnish measured before or after curing, the transmittance before curing was 96% and that after curing was 85%. This means that the change in transmittance was 11%. When the chemical resistance of the cured film was evaluated, the film dissolved completely.
- Into a 500-ml flask were charged 5 g of 2,2′-azobis(isobutyronitrile) and 200 g of tetrahydrofuran (THF). Then 35 g of methyl methacrylate (MM), 30 g of tert-butyl methacrylates (t-BM), and 35 g of methacrylic acid (MA) were charged and agitated at room temperature for a while, and after replacing the inside of the flask with nitrogen, agitation was done at room temperature for 40 hours. 300 g of propylene glycol monomethyl ether was added here and was agitated. After the completion of the agitation, the solution was charged into 2 L of water and a precipitate of a polymer solid was collected by filtration. Furthermore, washing with 2 L of water was done three times and the collected polymer solid was dried at 50° C. in a vacuum dryer for 72 hours, so that an acrylic resin was obtained.
- To 10 g of the obtained acrylic resin were added 4 g of 1,5-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compound (A-1) obtained in Synthesis Example 3, and 40 g of propylene glycol monomethyl ether acetate (PMA, available from Kuraray Co., Ltd.), so that a varnish of an acrylic resin composition was obtained. As to the transmittance at 450 nm of a film obtained using this varnish measured before or after curing, the transmittance before curing was 97% and that after curing was 93%. This means that the change in transmittance was 4%. When the chemical resistance of the cured film was evaluated, the film dissolved completely.
- 57.4 g (0.095 mol) of the hydroxyl group-containing diamine obtained in Synthesis Example 1 and 1.24 g (0.005 mol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane (SiDA) were dissolved in 200 g of NMP under dry nitrogen flow. 31.0 g (0.1 mol) of ODPA was added here and agitated at 40° C. for 2 hours. Then a solution in which 7.14 g (0.06 mol) of demethyl foramide dimethyl acetal (available from Mitsubishi Rayon Co., Ltd., DFA) had been diluted with 5 g of NMP was dropped over 10 minutes. After the dropping, agitation was continued at 40° C. for 2 hours. After the completion of the agitation, the solution was charged into 2 L of water and a precipitate of a polymer solid was collected by filtration. Furthermore, washing with 2 L of water was done three times and the collected polymer solid was dried at 50° C. in a vacuum dryer for 72 hours, so that a polyamide acid was obtained.
- A varnish of a polyimide precursor composition was obtained by weighing 10 g of the thus obtained polyamide acid and dissolving 2 g of 1,6-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.) and 4 g of MW-30HM (available from Sanwa Chemical Co., Ltd.) in 20 g of EL and 20 g of GBL. As to the transmittance at 450 nm of a film obtained using this varnish measured before or after curing, the transmittance before curing was 94% and that after curing was 40%. This means that the change in transmittance was 54%. The transmission spectra before and after curing are shown in
FIG. 3 . The transmittance of 400 nm to 550 nm dropped due to curing and therefore it was shown that coloring occurred clearly in the visible range. When the chemical resistance of the cured film was evaluated, the reduction in film thickness was 0.10 μm or less and therefore the chemical resistance was very good. - A varnish of a polyimide resin composition was prepared in the same manner as in Example 2 except for adding 10 g of the polyimide powder obtained in Example 1 instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 95% and that after curing was 45%. This means that the change in transmittance was 50%. When the chemical resistance of the cured film was evaluated, the reduction in film thickness was 0.1 μm or less and therefore the chemical resistance was very good.
- A varnish of a novolac resin composition was prepared in the same manner as in Example 2 except for using 10 g of a novolac resin PSF2808 (available from Gun Ei Chemical Industry Co., Ltd.) instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 97% and that after curing was 88%. This means that the change in transmittance was 9%. The transmission spectra before and after curing are shown in
FIG. 4 . The transmittance hardly dropped in the region of 400 nm or more after curing and therefore it was shown that coloring did not occurred in the visible range. When the chemical resistance of the cured film was evaluated, the film dissolved completely. - A varnish of a polyhydroxystyrene resin composition was prepared in the same manner as in Example 2 except for using 10 g of a polyhydroxystyrene resin MARUKA LYNCUR S-2 (available from Maruzen Petrochemical Co., Ltd.) instead of the polyamide acid and it was evaluated. It was found that as to the transmittance at 450 nm of a film measured before or after curing, the transmittance before curing was 97% and that after curing was 91%. This means that the change in transmittance was 6%.
- When the chemical resistance of the cured film was evaluated, the film dissolved completely.
- A varnish of a positive type photosensitive polyimide resin composition was obtained by further dissolving 4 g of the quinone diazide compound obtained in Synthesis Example 2 in the varnish of Example 1. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 95% before curing and 60% after curing. This means that the change in transmittance was 35%. The photosensitivity was 150 mJ/cm2. The reduction in film thickness was 0.10 μm or less. A pattern of 10 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was obtained by weighing 10 g of the polyamide acid obtained in Example 2 and dissolving 4 g of 1,7-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compound (A-2) obtained in Synthesis Example 4, and 4 g of the quinonediazide compound obtained in Synthesis Example 2 in 20 g of EL and 20 g of GBL. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 90% before curing and 59% after curing. This means that the change in transmittance was 31%. The photosensitivity was 150 mJ/cm2. The reduction in film thickness was 0.15 μm. A pattern of 10 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was prepared in the same manner as in Example 5 except for using 1-naphthol instead of 1,7-dihydroxynaphthalene and it was evaluated. The transmittance at 450 nm was 90% before curing and 77% after curing. This means that the change in transmittance was 13%. The reduction in film thickness was 0.20 μm. The photosensitivity was 300 mJ/cm2. A pattern of 20 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was prepared in the same manner as in Example 5 except for using 2,7-dihydroxynaphthalene instead of 1,7-dihydroxynaphthalene and it was evaluated. The transmittance at 450 nm was 90% before curing and 74% after curing. This means that the change in transmittance was 16%. The reduction in film thickness was 0.15 μm. The photosensitivity was 150 mJ/cm2. A pattern of 10 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was prepared by further dissolving, in the varnish of Example 5, 0.5 g of 5-propylsulfonyloxyimino-5H-thiophene-2-methylphenyl-acetonitrile (commercial name PAG-103, available from Ciba Specialty Chemicals Corporation) as a thermal acid generator. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 90% before curing and 59% after curing. This means that the decrease in transmittance was 31%. The photosensitivity was 150 mJ/cm2. The reduction in film thickness was 0.10 μm or less. A pattern of 10 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was obtained by further dissolving, in the varnish of Example 5, 0.5 g of the adhesion promoter (B-1) obtained in Synthesis Example 6. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 90% before curing and 59% after curing. This means that the change in transmittance was 31%. The photosensitivity was 150 mJ/cm2. The reduction in film thickness was 0.15 μm. A pattern of 3 μm or more remained.
- A varnish of a positive type photosensitive polyimide precursor composition was obtained by weighing 10 g of the polyamide acid obtained in Example 2 and dissolving 4 g of 2,3-dihydroxynaphthalene (available from Tokyo Chemical Industry Co. Ltd.), 5 g of the alkoxymethyl group-containing compound (A-2) obtained in Synthesis Example 4, and 4 g of the quinonediazide compound obtained in Synthesis Example 2 in 20 g of EL and 20 g of GBL. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 93% before curing and 63% after curing. This means that the change in transmittance was 30%. The reduction in film thickness was 0.15 μm. The photosensitivity was 200 mJ/cm2. A pattern of 10 μm or more remained.
- 18.3 g (0.05 mol) of BAHF was dissolved in 50 g of NMP and 26.4 g (0.3 mol) of glycidyl methyl ether under dry nitrogen flow and the temperature of the solution was cooled to −15° C. Here was dropped a solution in which 7.4 g (0.025 mol) of diphenyl ether dicarboxylic acid dichloride (available from Nihon Nohyaku Co., Ltd.) and 5.1 g (0.025 mol) of isophthalic acid chloride (available from Tokyo Chemical Industry Co. Ltd.) had been dissolved in 25 g of GBL so that the internal temperature might not exceed 0° C. After the completion of the dropping, agitation was continued at −15° C. for 6 hours. After the completion of the reaction, the solution was charged into 3 L of water containing 10% by weight of methanol and a white precipitate was collected. This precipitate was collected by filtration, washed with water three times, and then dried in a vacuum dryer of 50° C. for 72 hours, so that a polyhydroxyamide was obtained.
- A varnish of a positive type photosensitive polybenzoxazole precursor composition was obtained by dissolving 10 g of the obtained polyhydroxyamide, 4 g of 1,5-dihydroxynaphthalene, 2 g of the quinone diazide compound of Synthesis Example 2, 0.5 g of WPAG-314 (commercial name, available from Wako Pure Chemical Industries, Ltd.), and 5 g of MX-270 in 10 g of EL and 30 g of GBL. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 92% before curing and 61% after curing. This means that the decrease in transmittance was 31%. The reduction in film thickness was 0.25 μm and the photosensitivity was 160 mJ/cm2. A pattern of 20 μm or more remained.
- A varnish of a negative type photosensitive polybenzoxazole precursor composition was obtained by dissolving 10 g of the polyhydroxyamide obtained in Example 9, 1.5 g of 1,7-dihydroxynaphthalene, 0.5 g of WPAG-314 (commercial name, available from Wako Pure Chemical Industries, Ltd.), 0.5 g of 5-propylsulfonyloxyimino-5H-thiophene-2-methylphenyl-acetonitrile (commercial name PAG-103, available from Ciba Specialty Chemicals Corporation) as a thermal acid generator, and 2 g of MW-30HM in 40 g of GBL. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 95% before curing and 57% after curing. This means that the change in transmittance was 38%. The reduction in film thickness was 0.25 μm and the photosensitivity was 200 mJ/cm2. A pattern of 20 μm or more remained.
- A varnish of a negative type photosensitive polyimide resin composition was obtained by adding 5 g of 1,7-dihydroxynaphthalene, 4 g of the alkoxymethyl group-containing compounds (A-3) obtained in Synthesis Example 5, 2 g of ethyleneoxide-modified bisphenol A dimethacrylate (NK ester BPE-100, available from Shin-Nakamura Chemical Co., Ltd.), 0.5 g of trimethylolpropane triacrylate, 0.1 g of 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyloxime)](available from Ciba Specialty Chemicals Corporation), 20 g of EL, and 20 g of GBL to 10 g of the polyimide obtained in Example 1. Using the obtained varnish, the evaluation of the transmittance, the evaluation of the chemical resistance and the evaluation of the photosensitivity of a film before and after curing were performed as mentioned above. The transmittance at 450 nm was 94% before curing and 66% after curing. This means that the change in transmittance was 28%. The reduction in film thickness was 0.1 μm and the photosensitivity was 200 mJ/cm2. A pattern of 10 μm or more remained.
- The compositions and evaluation results of Examples 1 to 11 and Comparative Examples 1 to 6 are shown in Tables 1 to 3.
-
TABLE 1 Resin composition component Compound having two or more Fused polycyclic Thermal ethylenically aromatic compound cross- Photo acid unsaturated having a hydroxyl linking agent generator Photopolymerization bonds Resin group (Added (Added initiator (Added (Added amount) (Added amount) amount) amount) (Added amount) amount) Others Solvent Example 1 Polyimide 1,5- A-1 — — — — GBL (10 g) Dihydroxynaphthalene (5 g) (40 g) (4 g) Example 2 Polyamide acid 1,6- MW-30HM — — — — EL/GBL (10 g) Dihydroxynaphthalene (4 g) (20 g/20 g) (2 g) Example 3 Polyimide 1,6- MW-30HM — — — — EL/GBL (10 g) Dihydroxynaphthalene (4 g) (20 g/20 g) (2 g) Example 4 Polyimide 1,5- A-1 Synthesis — — — GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 (40 g) (4 g) (4 g) Example 5 Polyamide acid 1,7- A-2 Synthesis — — — EL/GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 (20 g/20 g) (4 g) (4 g) Example 6 Polyamide acid 1,7- A-2 Synthesis — — PAG-103 EL/GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 (0.5 g) (20 g/20 g) (4 g) (4 g) Example 7 Polyamide acid 1,7- A-2 Synthesis — — Adhesion EL/GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 promoter B-1 (20 g/20 g) (4 g) (4 g) (0.5 g) Example 8 Polyamide acid 2,3- A-2 Synthesis — — — EL/GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 (20 g/20 g) (4 g) (4 g) Example 9 Polyhydroxyamide 1,5- MX-270 Synthesis — — — EL/GBL (10 g) Dihydroxynaphthalene (5 g) Example 2 (10 g/30 g) (4 g) (2 g) WPAG- 314 (0.5 g) -
TABLE 2 Resin composition component Fused polycyclic aromatic compound having a hydroxyl Thermal cross- Photo acid Resin group linking agent generator (Added amount) (Added amount) (Added amount) (Added amount) Example 10 Polyhydroxyamide 1,7- MW-30HM WPAG-314 (10 g) Dihydroxynaphthalene (2 g) (0.5 g) (1.5 g) Example 11 Polyimide 1,7- A-3 — (10 g) Dihydroxynaphthalene (4 g) (5 g) Comparative Polyimide 1,5- 2,6- — Example 1 (10 g) Dihydroxynaphalene Dimethoxymethyl- (4 g) t-butylphenol(5 g) Comparative Acrylic resin 1,5- A-1 — Example 2 (10 g) Dihydroxynaphthalene (5 g) (4 g) Comparative Novolak resin 1,6 MW-30HM — Example 3 (10 g) Dihydroxynaphthalene (4 g) (2 g) Comparative Polyhydroxystyrene 1,6- MW-30HM — Example 4 (10 g) Dihydroxynaphthalene (4 g) (2 g) Comparative Polyamide acid 1-Naphthol A-2 Synthesis Example 2 Example 5 (10 g) (4 g) (5 g) (4 g) Comparative Polyamide acid 2,7- A-2 Synthesis Example 2 Example 6 (10 g) Dihydroxynaphthalene (5 g) (4 g) (5 g) Resin composition component Compound having two Photopolymerization or more ethylenically initiator unsaturated (Added amount) bonds(Added amount) Others Solvent Example 10 — — PAG-103 GBL (0.5 g) (40 g) Example 11 1,2-Octanedione-1[4- Ethoxylated bisphenol — EL/GBL (phenylthio)phenyl]-2- A dimethacrylate (2 g) (20 g/20 g) (o-benzoyloxime) (0.1 g) Trimethylolpropane triacrylate (0.5 g) Comparative — — GBL Example 1 (40 g) Comparative — — PMA Example 2 (40 g) Comparative — — EL/GBL Example 3 (20 g/20 g) Comparative — — EL/GBL Example 4 (20 g/20 g) Comparative — — EL/GBL Example 5 (20 g/20 g) Comparative — — EL/GBL Example 6 (20 g/20 g) -
TABLE 3 Transmittance Transmittance at Transmittance at Change in Chemical resistance 450 nm before 450 nm after transmittance at Remaining curing curing 450 nm Photosensitivity Loss of film pattern Example 1 95% 61% 34% — ≦0.10 μm — Example 2 94% 40% 54% — ≦0.10 μm — Example 3 95% 45% 50% — ≦0.10 μm — Example 4 95% 60% 35% 150 mJ/cm2 ≦0.10 μm 10 μm Example 5 90% 59% 31% 150 mJ/cm2 0.15 μm 10 μm Example 6 90% 59% 31% 150 mJ/cm2 ≦0.10 μm 10 μm Example 7 90% 59% 31% 150 mJ/cm2 0.15 μm 3 μm Example 8 93% 63% 30% 200 mJ/cm2 0.15 μm 10 μm Example 9 92% 61% 31% 160 mJ/cm2 0.25 μm 20 μm Example 10 95% 57% 38% 200 mJ/cm2 0.25 μm 20 μm Example 11 94% 66% 28% 200 mJ/cm2 0.10 μm 10 μm Comparative 96% 85% 11% — Completely — Example 1 dissolved Comparative 97% 93% 4% — Completely — Example 2 dissolved Comparative 97% 88% 9% — Completely — Example 3 dissolved Comparative 97% 91% 6% — Completely — Example 4 dissolved Comparative 90% 77% 13% 300 mJ/cm2 0.20 μm 20 μm Example 5 Comparative 90% 74% 16% 150 mJ/cm2 0.15 μm 10 μm Example 6 - A bottom gate type TFT was formed on a glass substrate and wiring (1.0 μm in height) connected to the TFT was formed. A dielectric film made of Si3N4 was formed so that the TFT and the wires might be covered therewith. Next, a contact hole was formed in this dielectric film.
- Moreover, a planarization film was formed on the dielectric film in order to planarize the irregularities of the TFT and the wires. The formation of the planarization film on the dielectric film was carried out by spin coating the varnish of the photosensitive polyimide precursor composition obtained in Example 5 onto the substrate, prebaking it on a hot plate at 120° C. for 3 minutes, then exposing and developing it, and then subjecting it to heat calcination at 250° C. for 60 minutes under air flow. The coating property at the time of coating the varnish was good and no development of wrinkles or cracks was found in the cured film obtained after the exposure, development and calcination. The average step height of the wires was 500 nm and the thickness of the produced planarization film was 2000 nm.
- Next, a top emission type organic EL element was formed on the resulting planarization film. First, a bottom electrode of ITO was formed on the planarization film by sputtering in connection with a wire via a contact hole. Then, a resist was coated, prebaked, and exposed through a mask of a desired pattern, thereby being developed. Pattern processing was carried out by wet etching using an ITO etchant and using the resist pattern as a mask. Then, the resist pattern was stripped using a resist stripping liquid (a mixed liquid of monoethanolamine and DMSO). The thus obtained bottom electrode corresponds to an anode of an organic EL element.
- Next, a dielectric layer shaped so that it might cover the bottom electrode was formed. For the dielectric layer was used similarly the varnish of the photosensitive polyimide precursor composition obtained in Example 5. By providing this dielectric layer it is possible to prevent short-circuit between the bottom electrode and an upper electrode to be formed in a subsequent step. The dielectric layer was patterned and was subjected to heating treatment at 250° C. for 60 minutes, so that a dielectric layer having a moderate absorption near a wavelength of 450 nm was formed.
- Moreover, a hole transporting layer, red, green, and blue organic light-emitting layers, and an electron transporting layer were provided one after another by vapor deposition via a desired pattern mask in a vacuum deposition apparatus. Subsequently, an upper electrode of aluminum was formed over the whole top surface of the substrate. This corresponds to a cathode of an organic EL element. The aforementioned substrate obtained was taken out of the vacuum deposition apparatus and then was sealed by bonding it to a sealing glass substrate using an ultraviolet-curable epoxy resin.
- In the above-described manner, an active-matrix type organic EL display device in which a TFT has been connected to each organic EL element for driving it was obtained. Good luminescence was exhibited when voltage was applied via a driving circuit.
- A bottom gate type TFT was formed on a glass substrate and wiring (1.0 μm in height) connected to the TFT was formed. A dielectric film made of Si3N4 was formed so that the TFT and the wires might be covered therewith. Next, a contact hole was formed in this dielectric film. This wiring is an item for connecting a TFT and another TFT or an organic EL element to be formed in a subsequent step and a TFT.
- Next, a bottom electrode of ITO was formed by sputtering in connection with a wire via a contact hole. Then, a resist was coated, prebaked, and exposed through a mask of a desired pattern, thereby being developed. Pattern processing was carried out by wet etching using an ITO etchant and using the resist pattern as a mask. Then, the resist pattern was stripped using a resist stripping liquid (a mixed liquid of monoethanolamine and DMSO). The thus obtained bottom electrode corresponds to an anode of an organic EL element.
- Next, a dielectric layer having such a shape that it could cover the periphery of the bottom electrode, the TFT, and the steps of the wires was formed. As to the dielectric layer, the varnish of the photosensitive polyimide precursor composition obtained in Example 5 was spin coated onto the substrate, subsequently dried under reduced pressure, then prebaked on a hot plate at 120° C. for 3 minutes, then exposed and developed, and then subjected to heat calcination at 250° C. for 60 minutes under nitrogen flow. The coating property at the time of spin coating the varnish was good and no development of wrinkles or cracks was found in the cured film obtained after the exposure, development and calcination. The average step height of the wires was 500 nm and the thickness of the produced dielectric layer was 2000 nm. By providing this dielectric layer it is possible to prevent short-circuit between the bottom electrode and an upper electrode to be formed in a subsequent step. Thus, an dielectric layer having a moderate absorption near a wavelength of 450 nm was formed.
- Moreover, a hole transporting layer, red, green, and blue organic light-emitting layers, and an electron transporting layer were provided one after another by vapor deposition via a desired pattern mask in a vacuum deposition apparatus. Subsequently, an upper electrode of aluminum was formed over the whole top surface of the substrate. This corresponds to a cathode of an organic EL element. The aforementioned substrate obtained was taken out of the vacuum deposition apparatus and then was sealed by bonding it to a sealing glass substrate using an ultraviolet-curable epoxy resin.
- In the above-described manner, an active-matrix type organic EL display device in which a TFT has been connected to each organic EL element for driving it was obtained. Good luminescence was exhibited when voltage was applied via a driving circuit.
- The resin composition of the present invention can be used suitably for applications such as a surface protective film and an interlayer dielectric film of a semiconductor element, a dielectric layer of an organic EL element, a planarization film of a TFT substrate for driving of a display device using an organic EL element, a wire-protecting dielectric film of a circuit board, an on-chip microlens of a solid imaging element, a planarization film for displays and solid imaging elements, a solder resist for circuit boards, an underfill agent, and a capping agent for preventing copper migration.
-
- 1: TFT
- 2: Wire
- 3: Dielectric film
- 4: Planarization film
- 5: ITO
- 6: Substrate
- 7: Contact hole
- 8: Dielectric layer
Claims (4)
—N(CH2OR6)t(H)v (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/202,595 US8895676B2 (en) | 2009-01-29 | 2014-03-10 | Resin composition and display device using the same |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009-017790 | 2009-01-29 | ||
JP2009017790 | 2009-01-29 | ||
PCT/JP2010/050402 WO2010087238A1 (en) | 2009-01-29 | 2010-01-15 | Resin composition and display device formed using same |
US201113146794A | 2011-08-09 | 2011-08-09 | |
US14/202,595 US8895676B2 (en) | 2009-01-29 | 2014-03-10 | Resin composition and display device using the same |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2010/050402 Division WO2010087238A1 (en) | 2009-01-29 | 2010-01-15 | Resin composition and display device formed using same |
US13/146,794 Division US8709552B2 (en) | 2009-01-29 | 2010-01-15 | Resin composition and display device using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
US20140191222A1 true US20140191222A1 (en) | 2014-07-10 |
US8895676B2 US8895676B2 (en) | 2014-11-25 |
Family
ID=42395499
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/146,794 Expired - Fee Related US8709552B2 (en) | 2009-01-29 | 2010-01-15 | Resin composition and display device using the same |
US14/202,595 Expired - Fee Related US8895676B2 (en) | 2009-01-29 | 2014-03-10 | Resin composition and display device using the same |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/146,794 Expired - Fee Related US8709552B2 (en) | 2009-01-29 | 2010-01-15 | Resin composition and display device using the same |
Country Status (7)
Country | Link |
---|---|
US (2) | US8709552B2 (en) |
JP (1) | JP5699602B2 (en) |
KR (1) | KR101596985B1 (en) |
CN (1) | CN102227474B (en) |
SG (1) | SG173468A1 (en) |
TW (1) | TWI464214B (en) |
WO (1) | WO2010087238A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200192227A1 (en) * | 2014-10-06 | 2020-06-18 | Toray Industries, Inc. | Resin composition, method for producing heat-resistant resin film, and display device |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5630175B2 (en) * | 2010-09-15 | 2014-11-26 | 東レ株式会社 | Photosensitive resin composition |
WO2012098828A1 (en) * | 2011-01-21 | 2012-07-26 | 三菱瓦斯化学株式会社 | Low molecular weight compound, radiation-sensitive composition, and method for forming resist pattern |
TWI422970B (en) * | 2011-03-21 | 2014-01-11 | Chi Mei Corp | Photosensitive resin composition, spacer and liquid crystal display device having thereof |
JP2012216454A (en) * | 2011-04-01 | 2012-11-08 | Seiko Epson Corp | Light-emitting device and electronic apparatus |
JP5928447B2 (en) * | 2011-08-18 | 2016-06-01 | 東レ株式会社 | Flexible substrate, display device and light receiving device |
WO2013125194A1 (en) * | 2012-02-23 | 2013-08-29 | 日立化成デュポンマイクロシステムズ株式会社 | Production method for display substrates |
WO2014073591A1 (en) * | 2012-11-08 | 2014-05-15 | 旭化成イーマテリアルズ株式会社 | Substrate for flexible device, flexible device and method for producing same, laminate and method for producing same, and resin composition |
JP6212979B2 (en) * | 2013-06-21 | 2017-10-18 | 東レ株式会社 | Resin composition |
JP6478051B2 (en) * | 2013-06-26 | 2019-03-06 | 日産化学株式会社 | Resist underlayer film forming composition comprising substituted crosslinkable compound |
JP6303588B2 (en) * | 2013-08-08 | 2018-04-04 | Jsr株式会社 | Radiation-sensitive resin composition, insulating film, method for forming the same, and organic EL device |
TWI490653B (en) * | 2013-09-10 | 2015-07-01 | Chi Mei Corp | Positive photosensitive resin composition and method for forming patterns by using the same |
JP6520091B2 (en) * | 2013-12-16 | 2019-05-29 | Jsr株式会社 | Colored composition, colored cured film and display device |
CN104167563B (en) * | 2014-08-15 | 2016-05-11 | 北京理工大学 | A kind of composite solid electrolyte film, preparation method and application |
KR20160092110A (en) * | 2015-01-26 | 2016-08-04 | 삼성디스플레이 주식회사 | Organic light emitting device |
US10896942B2 (en) * | 2015-03-11 | 2021-01-19 | Toray Industries, Inc. | Organic EL display device and method for manufacturing same |
CN107428935B (en) * | 2015-03-27 | 2019-04-02 | 东丽株式会社 | Diamine compound, heat-resistant resin or heat-resistant resin precursor using it |
SG11201708729TA (en) * | 2015-04-24 | 2017-11-29 | Toray Industries | Resin composition, method for manufacturing semiconductor element using same, and semiconductor device |
SG11201802076PA (en) * | 2015-09-30 | 2018-04-27 | Toray Industries | Negative photosensitive resin composition, cured film, element and display device each provided with cured film, and method for manufacturing display device |
US10324376B2 (en) * | 2015-09-30 | 2019-06-18 | Toray Industries, Inc. | Negative type colored photosensitive resin composition, cured film, element, and display device |
TWI559080B (en) * | 2015-11-09 | 2016-11-21 | 新應材股份有限公司 | Photosensitive insulating resin composition and method of producing insulating film thereof |
JP2017173741A (en) * | 2016-03-25 | 2017-09-28 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | Photosensitive siloxane composition |
KR102277707B1 (en) * | 2016-04-25 | 2021-07-16 | 도레이 카부시키가이샤 | resin composition |
TWI804465B (en) * | 2016-05-02 | 2023-06-11 | 日商三菱瓦斯化學股份有限公司 | Polyimide resin, polyimide resin composition, and polyimide film |
WO2018013342A1 (en) * | 2016-07-15 | 2018-01-18 | E. I. Du Pont De Nemours And Company | Electrically conductive adhesives |
JP6838369B2 (en) * | 2016-11-28 | 2021-03-03 | Hdマイクロシステムズ株式会社 | Negative photosensitive resin composition, curing pattern manufacturing method, cured product and electronic device |
KR20190085002A (en) * | 2016-11-30 | 2019-07-17 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | COMPOSITION, RESIN, COMPOSITION, RESIST PATTERN FORMING METHOD, |
CN109298600B (en) * | 2017-07-25 | 2022-03-29 | 台湾永光化学工业股份有限公司 | Amplified I-line photoresist composition |
US20200319549A1 (en) * | 2017-09-29 | 2020-10-08 | Toray Industries, Inc. | Photosensitive resin composition, cured film, element having cured film, organic el display, and method for manufacturing organic el display |
CN110221731B (en) * | 2018-03-02 | 2023-03-28 | 宸鸿光电科技股份有限公司 | Direct patterning method of touch panel and touch panel thereof |
KR102149966B1 (en) * | 2018-03-09 | 2020-08-31 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using the same and electronic device |
CN111094397B (en) * | 2018-07-20 | 2022-06-17 | 株式会社Lg化学 | Polyimide resin and negative photosensitive resin composition containing same |
JP7210999B2 (en) * | 2018-10-22 | 2023-01-24 | 東レ株式会社 | Resin composition, resin sheet, cured film, method for producing cured film, semiconductor device, and display device |
TWI685716B (en) * | 2019-01-11 | 2020-02-21 | 律勝科技股份有限公司 | Photosensitive polyimide resin composition and polyimide film thereof |
TWI685717B (en) * | 2019-01-11 | 2020-02-21 | 律勝科技股份有限公司 | Photosensitive resin composition and application thereof |
US20210109443A1 (en) * | 2019-01-23 | 2021-04-15 | Microcosm Technology Co., Ltd. | Photosensitive polyimide resin composition and polyimide film thereof |
US11572442B2 (en) * | 2020-04-14 | 2023-02-07 | International Business Machines Corporation | Compound, polyimide resin and method of producing the same, photosensitive resin composition, patterning method and method of forming cured film, interlayer insulating film, surface protective film, and electronic component |
WO2023153390A1 (en) * | 2022-02-14 | 2023-08-17 | 東レ株式会社 | Photosensitive resin sheet, cured film, and multilayer wiring substrate |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08134349A (en) * | 1994-11-02 | 1996-05-28 | Showa Highpolymer Co Ltd | Heat-resistant resin composition |
JPH08143670A (en) * | 1994-11-24 | 1996-06-04 | Showa Highpolymer Co Ltd | Heat resistant resin composition |
JP3807789B2 (en) * | 1996-08-23 | 2006-08-09 | 三井化学株式会社 | Photosensitive resin composition |
JPH10170715A (en) | 1996-12-12 | 1998-06-26 | Canon Inc | Production of resin black matrix, resin black matrix produced by the method, liquid crystal color filter having the black matrix, and liquid crystal panel using the color filter |
JP3913022B2 (en) | 2001-10-09 | 2007-05-09 | 旭化成エレクトロニクス株式会社 | Negative photosensitive resin composition |
SG135954A1 (en) | 2003-04-07 | 2007-10-29 | Toray Industries | Positive-type photosensitive resin composition |
WO2006098291A1 (en) * | 2005-03-15 | 2006-09-21 | Toray Industries, Inc. | Photosensitive resin composition |
JP4918968B2 (en) * | 2005-05-09 | 2012-04-18 | 日立化成デュポンマイクロシステムズ株式会社 | Positive photosensitive resin composition, pattern manufacturing method, and electronic component |
JP5044908B2 (en) * | 2005-09-02 | 2012-10-10 | 東レ株式会社 | Non-photosensitive resin composition and optical element using the same |
JP5338033B2 (en) * | 2006-05-31 | 2013-11-13 | 東レ株式会社 | Heat resistant resin composition, metal resin composite using the same, and electronic component |
JP2008122501A (en) | 2006-11-09 | 2008-05-29 | Sumitomo Chemical Co Ltd | Positive type radiation-sensitive resin composition |
JP2009227697A (en) * | 2008-03-19 | 2009-10-08 | Toray Ind Inc | Cross-linking agent and photosensitive resin composition using it |
JP2009258634A (en) | 2008-03-25 | 2009-11-05 | Toray Ind Inc | Positive photosensitive resin composition |
-
2010
- 2010-01-15 JP JP2010506056A patent/JP5699602B2/en active Active
- 2010-01-15 US US13/146,794 patent/US8709552B2/en not_active Expired - Fee Related
- 2010-01-15 SG SG2011054848A patent/SG173468A1/en unknown
- 2010-01-15 WO PCT/JP2010/050402 patent/WO2010087238A1/en active Application Filing
- 2010-01-15 KR KR1020117010340A patent/KR101596985B1/en active IP Right Grant
- 2010-01-15 CN CN2010800032835A patent/CN102227474B/en active Active
- 2010-01-25 TW TW099101926A patent/TWI464214B/en not_active IP Right Cessation
-
2014
- 2014-03-10 US US14/202,595 patent/US8895676B2/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200192227A1 (en) * | 2014-10-06 | 2020-06-18 | Toray Industries, Inc. | Resin composition, method for producing heat-resistant resin film, and display device |
US11640110B2 (en) * | 2014-10-06 | 2023-05-02 | Toray Industries, Inc. | Resin composition, method for producing heat-resistant resin film, and display device |
Also Published As
Publication number | Publication date |
---|---|
JPWO2010087238A1 (en) | 2012-08-02 |
US8895676B2 (en) | 2014-11-25 |
TWI464214B (en) | 2014-12-11 |
US20110284855A1 (en) | 2011-11-24 |
SG173468A1 (en) | 2011-09-29 |
TW201035241A (en) | 2010-10-01 |
CN102227474B (en) | 2013-11-06 |
CN102227474A (en) | 2011-10-26 |
WO2010087238A1 (en) | 2010-08-05 |
KR20110107793A (en) | 2011-10-04 |
JP5699602B2 (en) | 2015-04-15 |
KR101596985B1 (en) | 2016-02-23 |
US8709552B2 (en) | 2014-04-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8895676B2 (en) | Resin composition and display device using the same | |
KR101227280B1 (en) | Photosensitive resin composition and method for producing photosensitive resin film | |
TWI710584B (en) | Polyimide resin, polyimide resin composition, touch panel using the same and manufacturing method thereof, color filter and manufacturing method thereof, liquid crystal element and manufacturing method thereof, organic EL element and manufacturing method thereof | |
JP6332022B2 (en) | Photosensitive resin composition, heat-resistant resin film manufacturing method, and display device | |
TWI688826B (en) | Photosensitive colored resin composition, method for manufacturing heat-resistant colored resin film, and display device | |
KR102510370B1 (en) | Resin composition, method for producing heat-resistant resin film, and display device | |
JP5211438B2 (en) | Resin composition and display device using the same | |
US11086219B2 (en) | Negative-type photosensitive resin composition, cured film, display device that includes the cured film, and production method therefor | |
TWI725250B (en) | Resin composition, resin sheet, cured film, organic EL display device, semiconductor electronic part, semiconductor device, and method of manufacturing organic EL display device | |
KR102489060B1 (en) | Heat-resistant resin composition, method for producing a heat-resistant resin film, method for producing an interlayer insulating film or surface protective film, and method for producing electronic components or semiconductor components | |
JP6212979B2 (en) | Resin composition | |
JP6286834B2 (en) | Heat resistant resin composition and method for producing heat resistant resin film | |
JP2008039961A (en) | Positive photosensitive resin composition and organic electroluminescence device using the same | |
KR101354640B1 (en) | Positive type photosensitive resin composition | |
KR20190020016A (en) | Photosensitive resin composition, photosensitive sheet, cured film, element, organic EL display device, semiconductor electronic component, semiconductor device and manufacturing method of organic EL display device | |
KR20130078782A (en) | Positive type photosensitive resin composition | |
JP6903916B2 (en) | Resin composition | |
KR20140086724A (en) | Photosensitive resin composition for insulating film of display device, insulating film using the same, and display device using the same | |
JP2020101690A (en) | Method for forming bank pattern |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551) Year of fee payment: 4 |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
LAPS | Lapse for failure to pay maintenance fees |
Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20221125 |